The Stereoselective Total Synthesis
of Aculeatin A and B via Prins Cyclization

J. S. Yadav; N. Thrimurtulu; M. Venkatesh; A. R. Prasad

doi:10.1055/s-0029-1217144

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Synthesis 2010(3): 431-436
DOI: 10.1055/s-0029-1217144

PAPER

The Stereoselective Total Synthesis of Aculeatin A and B via Prins Cyclization

J. S. Yadav*, N. Thrimurtulu, M. Venkatesh, A. R. Prasad
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Further Information

Publication History

Received 26 August 2009
Publication Date:
27 November 2009 (online)

Abstract
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Abstract

The total synthesis of aculeatins A and B is described proving the versatility of Prins cyclization in natural product synthesis. The approach is convergent and highly stereoselective. Morpholine amide coupling with an alkyne and PIFA-mediated oxidative spirocyclization were utilized as key steps.

Key words

aculeatins - Prins cyclization - morpholine amide - PIFA-mediated oxidative spirocyclization

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