Synthetic studies of the lichen macrolide lepranthin. Stereoselective synthesis of the diolide framework based on regioselective epoxide-opening reactions.

Abstract:

:Stereoselective synthesis of the 16-membered diolide 27, a fully functionalized congener of lepranthin (1), is described. The requisite five asymmetric carbon centers in monomer 23 were constructed in a highly stereoselective manner by using different epoxide-opening reactions of α,β-unsaturated γ,δ-epoxy esters and epoxy alcohol derivatives as the key steps. The monomer 23 was successfully transformed into the MOM protected diolide 27 by Yamaguchi macrolactonization.

authors

Takada H,Nagumo S,Yasui E,Mizukami M,Miyashita M

doi

10.1248/cpb.59.525

subject

Has Abstract

pub_date

2011-01-01 00:00:00

pages

525-7

issue

4

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/59.525

journal_volume

59

pub_type

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