The Discreet Structural Diversity of Briarellins: DU8+ Guided Multiple Structure Revisions Yielded Two Unknown Structural Types

Briarellins, a subset of C2–C11 cyclized cembranoids, were proposed to contain a C3–C14 ether or lactone bridge, similar to asbestinins. However, the total synthesis of the proposed structure of briarellin J revealed a misassignment. We revisited briarellins, computationally, with the help of a rece...

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Veröffentlicht in:	Journal of organic chemistry 2020-05, Vol.85 (9), p.6201-6205
Hauptverfasser:	Holt, Tina A, Reddy, D. Sai, Huple, Deepak B, West, Lyndon M, Rodríguez, Abimael D, Crimmins, Michael T, Kutateladze, Andrei G
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Sprache:	eng
Schlagworte:	Chemistry Chemistry, Organic Lactones Physical Sciences Science & Technology
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creator	Holt, Tina A Reddy, D. Sai Huple, Deepak B West, Lyndon M Rodríguez, Abimael D Crimmins, Michael T Kutateladze, Andrei G
description	Briarellins, a subset of C2–C11 cyclized cembranoids, were proposed to contain a C3–C14 ether or lactone bridge, similar to asbestinins. However, the total synthesis of the proposed structure of briarellin J revealed a misassignment. We revisited briarellins, computationally, with the help of a recently developed hybrid DFT/parametric method, DU8+, and revised the structures of briarellin C14–C3 ε-lactones to new structural types containing either a C14–C11 or C14–C12 lactone bridge. The original structures of briarellin and asbestinin ethers were confirmed.
doi_str_mv	10.1021/acs.joc.0c00555
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subjects	Chemistry Chemistry, Organic Lactones Physical Sciences Science & Technology
title	The Discreet Structural Diversity of Briarellins: DU8+ Guided Multiple Structure Revisions Yielded Two Unknown Structural Types
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