General Approach to 2,3-Dibenzyl-γ-butyrolactone Lignans: Application to the Total Synthesis of (±)-5′-Methoxyyatein, (±)-5′-Methoxyclusin, and (±)-4′-Hydroxycubebinone

The total synthesis of natural lignans 5′‐methoxyyatein (1), 5′‐methoxyclusin (2), and 4′‐hydroxycubebinone (3), in racemic form, has been achieved by a newly developed strategy, wherein lithium naphthalenide induced decyanation was employed as a key operation to establish the essential trans config...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2010-06, Vol.2010 (18), p.3473-3480
Main Authors: Amancha, Prashanth K., Liu, Hsing-Jang, Ly, Tai Wei, Shia, Kak-Shan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones
Lignans
Natural products
Organic chemistry
Preparations and properties
Synthetic ­methods
Total synthesis
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Summary:The total synthesis of natural lignans 5′‐methoxyyatein (1), 5′‐methoxyclusin (2), and 4′‐hydroxycubebinone (3), in racemic form, has been achieved by a newly developed strategy, wherein lithium naphthalenide induced decyanation was employed as a key operation to establish the essential trans configuration of the butyrolactone ring. A concise synthetic route to the 2,3‐dibenzylbutyrolactone core has been developed, whereby the total synthesis of natural lignans 1, 2, and 3, in racemic form, in an overall yield of 25, 18, and 19 %, respectively, has been accomplished.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201000318