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Synthesis 2012(2): 311-315  
DOI: 10.1055/s-0031-1289640
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Concise Total Synthesis of Leodomycin C and D

B. Chinnababu, S. Purushotham Reddy, D. Kumar Reddy, D. Chandra Rao, Y. Venkateswarlu*
Organic Chemistry Division-I, Natural Products Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
Fax: +91(40)27160512; e-Mail: luchem@iict.res.in;
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Publication History

Received 10 October 2011
Publication Date:
08 December 2011 (online)

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Abstract

Stereoselective concise total synthesis of leodomycin C and D from commercially available propylene oxide using Jacobsen’s hydrolytic kinetic resolution (HKR), base-promoted alkyne zipper reaction, TPP-promoted enyne ester (ynoate) to diene ester (dienoate) isomerization, and (R)-(+)-2-methyl-CBS-oxazaborolidine reduction as key steps is reported.

Key words

Bacillus sp - leodomycin C and D - antimicrobial activity - hydrolytic kinetic resolution - HKR - alkyne zipper reaction - (R)-(+)-2-methyl-CBS-oxazaborolidine

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