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Synthesis 2010(15): 2521-2526  
DOI: 10.1055/s-0029-1218831
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantiodivergent Formal Total Synthesis of Aspercyclide C from l-(+)-Tartaric Acid

Kavirayani R. Prasad*, Vasudeva Rao Gandi, John Eugene Nidhiry, Kavya S. Bhat
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
Fax: +91(80)23600529; e-Mail: prasad@orgchem.iisc.ernet.in;
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Publication History

Received 1 March 2010
Publication Date:
18 June 2010 (online)

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Abstract

The enantiodivergent formal syntheses of both enantio­mers of aspercyclide C is accomplished. Starting from l-(+)-tartaric acid, the key protected allylic alcohol, (3R,4R)-4-(methoxy­methoxy)non-1-en-3-ol is prepared, and is then elaborated into both enantiomers of 3-[(4-methoxybenzyl)oxy]non-1-en-4-ol via Mitsunobu­ inversion. Esterification with a known biaryl acid, followed by ring-closing metathesis and deprotection completes the syntheses.

Key words

aspercyclide C - total synthesis - tartaric acid - Mitsunobu inversion - ring-closing metathesis

6

Formation of the other diastereomer was not detected within the limits of ¹H NMR spectroscopy.

10

Biaryl acid 5 was prepared according to the method of Ramana et al., see ref. 2d.