Formal total synthesis of (-)-kumausallene

TitleFormal total synthesis of (-)-kumausallene
Publication TypeJournal Article
Year of Publication2015
AuthorsDas, S, Ramana, CV
JournalTetrahedron
Volume71
Issue45
Pagination8577-8584
Date PublishedNOV
ISSN0040-4020
KeywordsBis-THF natural products, Chiral pool, Deacetylkumausyne, Total synthesis, Wittig reaction
Abstract

Deacetylkumausyne-a penultimate intermediate in Tang'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'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's group). Thus, this overall exercise has culminated in a formal total synthesis of (-)-kumausallene. (C) 2015 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2015.09.027
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.645
Divison category: 
Organic Chemistry