EMAIL THIS PAGE TO A FRIEND

Organic letters

Short total syntheses of both the putative and actual structures of the clerodane diterpenoid (+/-)-sacacarin by double annulation.


PMID 11735576

Abstract

[reaction: see text] The putative structure of the naturally occurring clerodane diterpenoid (+/-)-sacacarin has been prepared in only 10 steps, six of which are C-C bond-forming steps, in a chemo-, regio-, and diastereoselective manner. The key part of the synthesis is the double annulation (double Michael, Pinner, and Dieckmann reaction) of a tethered carbon diacid and 3-butyn-2-one. A corrected structure for sacacarin is proposed, and the structure is proven by synthesis.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

161314
3-Butyn-2-one, 95%
C4H4O