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Synlett 2023; 34(01): 67-72
DOI: 10.1055/a-1957-3966
letter

Asymmetric Total Synthesis of (2E)-Macrolactin 3

Aedula Vishnu V. Reddy
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Utkal Mani Choudhury
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Akella V. S. Sarma
b   Centre for NMR and Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Debendra K. Mohapatra∗
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
c   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
› Author AffiliationsThe authors gratefully acknowledge the financial support received from the Department of Science and Technology-Science and Engineering Research Board (DST-SERB), New Delhi, India (Grant No. EMR/2017/002298). A.V.V.R. and U.M.C. thank the University Grants Commission (UGC), New Delhi, India, for financial assistance in the form of fellowships.
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Dedicated to Dr. Mukund K. Gurjar on the occasion of his 70th birthday

Abstract

Asymmetric total synthesis of (2E)-macrolactin 3 has been accomplished in a highly convergent manner utilizing our earlier developed tandem isomerization followed by C–O and C–C bond-forming reaction, Sharpless asymmetric dihydroxylation, and a late-stage intramolecular Heck coupling reaction. Comparison of the NMR spectra of the coupled product and thorough analysis of the 2D NMR data of the final compound led to the conclusion that the Z-double bond at C2 was isomerized during the coupling reaction.

Key words

macrolactin - natural products - asymmetric synthesis - isomerization/C–O/C–C - Heck coupling

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1957-3966.
  • Supporting Information


Publication History

Received: 01 September 2022

Accepted after revision: 07 October 2022

Accepted Manuscript online:
07 October 2022

Article published online:
15 November 2022

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