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. 2009;48(29):5334-6.
doi: 10.1002/anie.200901669.

Total synthesis of cyathin A(3) and cyathin B(2)

Keunho Kim  1 , Jin Kun Cha
Affiliations

Total synthesis of cyathin A(3) and cyathin B(2)

Keunho Kim et al. Angew Chem Int Ed Engl. 2009.

Abstract

A stereoselective synthesis of cyathin A(3) and cyathin B(2) has been achieved by a Prins-type reaction of a cycloalkenyl cyclopropanol. Particularly noteworthy is the use of a spirocyclobutanone moiety as a convenient scaffold for an efficient ring-closing metathesis to stereoselectively construct a suitably functionalized seven-membered ring (see scheme).

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Figures

Scheme 1
Scheme 1
Retrosynthetic analysis.
Scheme 2
Scheme 2
Construction of the tricyclic core.
Scheme 3
Scheme 3
Total synthesis of cyathin B2 (2).
Scheme 4
Scheme 4
Total synthesis of cyathin A3 (1).
See this image and copyright information in PMC

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