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
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
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Experimental details, analytical data, 1H and 13C NMR data (PDF)
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