Synthesis 2013; 45(2): 251-259
DOI: 10.1055/s-0032-1317700
paper
© Georg Thieme Verlag Stuttgart · New York

Studies toward the Total Synthesis of Carolacton

Gowravaram Sabitha*
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160512   Email: gowravaramsr@yahoo.com   Email: sabitha@iict.res.in
,
K. Shankaraiah
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160512   Email: gowravaramsr@yahoo.com   Email: sabitha@iict.res.in
,
M. Nagendra Prasad
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160512   Email: gowravaramsr@yahoo.com   Email: sabitha@iict.res.in
,
Jhillu S. Yadav
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160512   Email: gowravaramsr@yahoo.com   Email: sabitha@iict.res.in
› Author Affiliations
Further Information

Publication History

Received: 26 September 2012

Accepted after revision: 07 November 2012

Publication Date:
17 December 2012 (online)


Abstract

An efficient synthesis of the C1–C19 segment of carolacton is described, starting from d-ribose, (–)-β-citronellene and a homopropargylic alcohol, and which employs a Nozaki–Hiyama–Kishi (NHK) coupling as the key step. Other important steps are cross-metathesis and Evans aldol reactions.

Supporting Information

 
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