Chemoenzymatic collective synthesis of optically active hydroxyl(methyl)tetrahydronaphthalene-based bioactive terpenoids

TitleChemoenzymatic collective synthesis of optically active hydroxyl(methyl)tetrahydronaphthalene-based bioactive terpenoids
Publication TypeJournal Article
Year of Publication2015
AuthorsBatwal, RU, Argade, NP
JournalOrganic & Biomolecular Chemistry
Volume13
Issue46
Pagination11331-11340
Date PublishedSEP
ISSN1477-0520
Abstract

Starting from succinic anhydride and 2-methylanisole, a chemoenzymatic collective formal/total synthesis of several optically active tetrahydronaphthalene based bioactive natural products has been presented via advanced level common precursors; the natural product and antipode (-)/(+)-aristelegone B. Regioselective benzylic oxidations, stereoselective introduction of hydroxyl groups at the alpha-position of ketone moiety in syn-orientation, efficient enzymatic resolutions with high enantiomeric purity, stereoselective reductions, samarium iodide induced deoxygenations and tandem acylation-Wittig reactions without racemization and/or eliminative aromatization were the key features. An attempted diastereo-selective synthesis of (+/-)-vallapin has also been described.

DOI10.1039/c5ob01740h
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)3.559
Divison category: 
Organic Chemistry