Synthesis of the C1 -C10 Fragment of Muamvatin

Anandaraju Bandaru; Krishna P Kaliappan

doi:10.1002/asia.202000459

Synthesis of the C₁ -C₁₀ Fragment of Muamvatin

Chem Asian J. 2020 Jul 16;15(14):2208-2211. doi: 10.1002/asia.202000459. Epub 2020 Jun 12.

Authors

Anandaraju Bandaru^{1

1}, Krishna P Kaliappan^{1

1}

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400076, India.

PMID: 32432834
DOI: 10.1002/asia.202000459

Abstract

This report delineates our efforts towards the synthesis of a stereochemically well-defined ketone, the C₁ -C₁₀ fragment of muamvatin, the first example of a 2, 4, 6-trioxaadamantane ring skeletal polypropionate marine natural product, using two non-aldol variants. i) The Shimizu reaction, a Pd(0) mediated stereoselective epoxy-ring opening of alkenyl oxiranes, was employed for the stereoselective installation of methyl groups in syn-fashion and ii) Bode's protocol, a NHC-mediated reaction on β-epoxy aldehydes, was utilized for stereoselective construction of methyl and hydroxyl groups in anti-fashion.

Keywords: Bode's protocol; Marine natural product; Shimizu reaction; muamvatin; non-aldol strategy.

Abstract

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