Synlett 2019; 30(11): 1346-1350
DOI: 10.1055/s-0037-1611559
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a C1–C12 Fragment of Gulmirecin B

Rathikrishnan Rengarasu
,
Financial support by the state of Baden-Württemberg is gratefully acknowledged.
Further Information

Publication History

Received: 14 February 2019

Accepted after revision: 03 May 2019

Publication Date:
22 May 2019 (online)


Abstract

The synthesis of a C1–C14 fragment of the macrolide antibiotic gulmirecin B through formation of the C7–C8 bond by addition of a vinyllithium intermediate to a C1–C7 aldehyde was investigated. This crucial coupling was successful with a vinyllithium reagent corresponding to a C8–C12 fragment. The C8–C12 vinyl bromide was prepared from l-malic acid. The C1–C7 aldehyde building block was synthesized from hex-5-enoic acid by using an Evans alkylation, a cross-metathesis, and an asymmetric dihydroxylation as key steps.

Supporting Information

 
  • References and Notes

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