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A Unified Strategy to Access Trans-Syn-Fused Drimane Meroterpe-noids: Chemoenzymatic Total Syntheses of Polysin, N-Acetyl-Polyveoline and the Chrodrimanins

13 August 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Trans-syn-fused drimane meroterpenoids are unique natural products that arise from contra-thermodynamic polycyclizations of their polyene precursors. Herein we report the first total syntheses of four trans-syn-fused drimane meroterpenoids, namely polysin, N-acetyl-polyveoline, chrodrimanin C and verruculide A in 7–18 steps from sclareolide. The trans-syn-fused drimane unit is accessed through an efficient acid-mediated C9 epimerization of sclareolide. Subsequent applications of enzy-matic C–H oxidation and contemporary annulation methodologies install the requisite C3 hydroxyl group and enable rapid gen-eration of structural complexity to provide concise access to these natural products.

Supplementary materials

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Title
Supporting Information for A Unified Strategy to Access Trans-Syn-Fused Drimane Meroterpe-noids: Chemoenzymatic Total Syntheses of Polysin, N-Acetyl-Polyveoline and the Chrodrimanins
Description
Experimental details, analytical data, 1H and 13C NMR data (PDF)
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Version History

Aug 13, 2021 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-2s4hl
D O I: 10.26434/chemrxiv-2021-2s4hl [opens in a new tab]

Funding

National Science Foundation
1945468

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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