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. 2006 May 11;8(10):2123-6.
doi: 10.1021/ol0605777.

Synthesis of ent-thallusin

Xiaolei Gao  1 , Yoshihide Matsuo, Barry B Snider
Affiliations

Synthesis of ent-thallusin

Xiaolei Gao et al. Org Lett. .

Abstract

[reaction: see text] A three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(I) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.

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Figures

Scheme 1
Scheme 1
Retrosynthesis of Thallusin (1)
Scheme 2
Scheme 2
Preparation of 2 and 4
Scheme 3
Scheme 3
Preparation of 4 and 5
Scheme 4
Scheme 4
Synthesis of ent-thallusin (1)
See this image and copyright information in PMC

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