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Angew Chem Int Ed Engl. 2015 Aug 3;54(32):9319-22. doi: 10.1002/anie.201503818. Epub 2015 Jun 18.

Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid.

Author information

1
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084 (USA).
2
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084 (USA). negishi@purdue.edu.

Abstract

A new strategy for highly concise, convergent, and enantioselective access to polydeoxypropionates has been developed. ZACA-Pd-catalyzed vinylation was used to prepare smaller deoxypropionate fragments, and then two key sequential Cu-catalyzed stereocontrolled sp(3)-sp(3) cross-coupling reactions allowed convergent assembly of smaller building blocks to build-up long polydeoxypropionate chains with excellent stereoselectivity. We employed this strategy for the synthesis of phthioceranic acid, a key constituent of the cell-wall lipid of Mycobacterium tuberculosis, in just 8 longest linear steps with full stereocontrol.

KEYWORDS:

ZACA reaction; asymmetric synthesis; cross-coupling; natural product synthesis; polydeoxypropionates

PMID:
26088188
DOI:
10.1002/anie.201503818
[Indexed for MEDLINE]

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