@article { ISI:000261546900021, title = {Suzuki cross-coupling and intramolecular aza-michael addition reaction sequence towards the synthesis of 1,10b-epi-7-deoxypancratistatins and their cytotoxicity studies}, journal = {European Journal of Organic Chemistry}, number = {34}, year = {2008}, month = {DEC}, pages = {5839-5847}, publisher = {WILEY-V C H VERLAG GMBH}, type = {Article}, address = {PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY}, abstract = {

The development of an efficient approach to the construction of a phenanthridone is described. The convergent strategy commences with the preparation of Suzuki cross-coupling reaction precursors, arylboronic acid 12 and a-iodo enone 14, from piperonylamine (9) and (-)-D-quinic acid (10), respectively. The coupling of 12 and 19 followed by a key intramolecular aza-Michael addition produced phenanthridone 21 featuring a cis-fused B-C ring junction. The syntheses of compounds 25 and 26, both of which are C-1 and C-10b epimers of the naturally occurring potent antitumor agent 7-deoxypancratistatin (2), from 21 are elaborated in detail in this paper. The cytotoxicities of 25 and 26 were evaluated against three different cancer cell lines. Compound 26 served as a moderate growth inhibitor of THP-1 monocytic cells (GI(50) = 14.5 mu g/mL). ((C) Wiley-VCH Verlag GmbH \& Co. KGaA, 69451 Weinheim, Germany, 2008)

}, keywords = {antitumor agents, Chiral pool, Cross-coupling, Intramolecular aza-Michael addition, Pancratistatin}, issn = {1434-193X}, doi = {10.1002/ejoc.200800830}, author = {Pandey, Ganesh and Balakrishnan, Madhesan and Swaroop, Pandrangi Siva} } @article { ISI:000287801700007, title = {Synthetic studies of superstolide A: a carbohydrate based synthesis of the C21-C26 segment}, journal = {Letters in Organic Chemistry}, volume = {7}, number = {8}, year = {2010}, month = {DEC}, pages = {657-660}, publisher = {BENTHAM SCIENCE PUBL LTD}, address = {EXECUTIVE STE Y26, PO BOX 7917, SAIF ZONE, 1200 BR SHARJAH, U ARAB EMIRATES}, abstract = {

The synthesis of C21-C26 fragment of superstolide A, starting from D-glucose diacetonide, involving regioselective ring opening of epoxide by Grignard reagent and regioselective stereospecefic hydroboration oxidation has been described.

}, keywords = {Chiral pool, Potent cytotoxic, Regioselective epoxide opening, Stereoselective hydroboration-oxidation, Superstolide A}, issn = {1570-1786}, doi = {10.2174/157017810793811704}, author = {Pal, Rita and Rahaman, Hasibur and Mohapatra, Debendra K. and Gurjar, Mukund K.} } @article { ISI:000288074100009, title = {Stereoselective synthesis of (-)-galantinic acid}, journal = {Synthesis-Stuttgart}, number = {6}, year = {2011}, month = {MAR}, pages = {901-904}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

An efficient and highly concise synthesis of (-)-galantinic acid has been achieved using an asymmetric allylation reaction of Garner{\textquoteright}s aldehyde.

}, keywords = {Amino alcohol, Chiral pool, iterative asymmetric allylation, Oxidation, stereoselective synthesis}, issn = {0039-7881}, doi = {10.1055/s-0030-1258431}, author = {Dubey, Abhishek and Harbindu, Anand and Kumar, Pradeep} } @article { ISI:000304037200008, title = {Carbohydrate based total synthesis of xestodecalactone B and C: revision of the absolute configuration}, journal = {Current Organic Chemistry}, volume = {16}, number = {9}, year = {2012}, month = {MAY}, pages = {1159-1168}, publisher = {BENTHAM SCIENCE PUBL LTD}, address = {EXECUTIVE STE Y26, PO BOX 7917, SAIF ZONE, 1200 BR SHARJAH, U ARAB EMIRATES}, abstract = {

A convergent chiral pool approach for the total synthesis of xestodecalactones B and C was demonstrated in which intramolecular acylation reaction constituted the key step. Synthetic and spectroscopic studies reported herein, suggested that the previously assigned structures of xestodecalactone B and C be interchanged.

}, keywords = {Chiral pool, Hydroboration, Intramolecular acylation, Pinnick oxidation, Revision of absolute configuration, Xestodecalactone B and C}, issn = {1385-2728}, author = {Pal, Rita and Rahaman, Hasibur and Gurjar, Mukund K.} } @article { ISI:000336248900015, title = {Total synthesis of the putative structure of xylarinol B}, journal = {Chemistry-An Asian Journal}, volume = {9}, number = {6}, year = {2014}, month = {JUN}, pages = {1557-1562}, publisher = {WILEY-V C H VERLAG GMBH}, address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY}, abstract = {

The total synthesis of the putative structure of xylarinolB is described and the need to revise its structure is demonstrated. The central benzoxepine skeleton was constructed by employing a cobalt-mediated bimolecular [2+2+2] Reppe-Vollhardt alkyne cycloaddition reaction.

}, keywords = {Chiral pool, cobalt, Natural products, structure elucidation, Total synthesis}, issn = {1861-4728}, doi = {10.1002/asia.201301647}, author = {More, Atul A. and Ramana, Chepuri V.} } @article {45947, title = {Chirality induction and chiron approaches to enantioselective total synthesis of alpha-lipoic acid}, journal = {Tetrahedron}, volume = {71}, year = {2015}, month = {JUN }, pages = {4213-4218}, type = {Article}, abstract = {

An efficient, short and convenient asymmetric synthesis of (R)-(+)-lipoic acid in seven steps from chiral hydroxy aldehyde with 32.5\% overall yield is described. Synthesis of S and R enantiomers of a-lipoic acid from cis-1,4-butene diol derived chiral lactone is reported with 34 \% overall yield. The present synthesis involves use of simple reaction conditions making it a convenient synthesis. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {Chiral pool, Chirality induction, enantioselective, Lipoic acid, sharpless asymmetric dihydroxylation}, issn = {0040-4020}, doi = {10.1016/j.tet.2015.04.090}, author = {Chavan, Subhash P. and Pawar, Kailash P. and Praveen, Ch and Patil, Niteen B.} } @article { ISI:000363080800011, title = {Formal total synthesis of (-)-kumausallene}, journal = {Tetrahedron}, volume = {71}, number = {45}, year = {2015}, month = {NOV}, pages = {8577-8584}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Deacetylkumausyne-a penultimate intermediate in Tang{\textquoteright}s total synthesis of (-)-kumausallene has been synthesized employing a chiral pool approach and thus culminating in a formal total synthesis of kumausallene. The opening of an epoxide with alkyne (use of Birch reduction for the selective construction of E-pent-3-enyl group) and C-allylation have been used to introduce the pendant alkenyl side chains. Initial attempts to execute an alternative to Tang{\textquoteright}s route comprising a prior installation of the bromoallene unit via bromoetherification and subsequent S(N)2 displacement are unsuccessful. To overcome this, an alternative approach was developed to arrive at Deacetylkumausyne (another natural product that has been synthesized and characterized by Tang{\textquoteright}s group). Thus, this overall exercise has culminated in a formal total synthesis of (-)-kumausallene. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {Bis-THF natural products, Chiral pool, Deacetylkumausyne, Total synthesis, Wittig reaction}, issn = {0040-4020}, doi = {10.1016/j.tet.2015.09.027}, author = {Das, Shyamsundar and Ramana, Chepuri V.} } @article { ISI:000382768400020, title = {Total synthesis of (-)-nardoaristolone B}, journal = {European Journal of Organic Chemistry}, number = {22}, year = {2016}, month = {AUG}, pages = {3804-3808}, publisher = {WILEY-V C H VERLAG GMBH}, address = {POSTFACH 101161, 69451 WEINHEIM, GERMANY}, abstract = {

A stereoselective total synthesis of (-)-Nardoaristolone B, a nor-aristolane sesquiterpenoid natural product with an unusual 3/5/6 tricyclic ring system is described. The highlights of the present work includes use of (+)-(R)-Pulegone as a chiral-pool starting material, ring-closing metathesis, allylic oxidation and stereoselective cyclopropanation. In addition, a new analogue of Nardoaristolone B (minor product from the final step) was isolated in pure form and fully characterized with the help of single-crystal X-ray analysis.

}, keywords = {Chiral pool, cyclopropanation, Nardoaristolone B, Natural products, Total synthesis}, issn = {1434-193X}, doi = {10.1002/ejoc.201600538}, author = {Ople, Rohini S. and Handore, Kishor L. and Kamat, Nidhi S. and Reddy, D. Srinivasa} }