Total Synthesis of (−)-Nemorosone and (+)-Secohyperforin

Total Synthesis of (−)-Nemorosone and (+)-Secohyperforin

A general strategy for the synthesis of polycyclic polyprenylated acylphloroglucinols is described in which a scalable, Lewis acid catalyzed epoxide-opening cascade cyclization is used to furnish common intermediate 4. The utility of this approach is exemplified by the total syntheses of both ent-ne...

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Veröffentlicht in:Organic letters 2015-07, Vol.17 (14), p.3398-3401
Hauptverfasser: Sparling, Brian A, Tucker, James K, Moebius, David C, Shair, Matthew D
Format: Artikel
Sprache:eng
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Benzophenones - chemical synthesis
Benzophenones - chemistry
Cyclization
Epoxy Compounds - chemistry
Lewis Acids - chemistry
Molecular Structure
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemical synthesis
Phloroglucinol - chemistry
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
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container_end_page 3401
container_issue 14
container_start_page 3398
container_title Organic letters
container_volume 17
creator Sparling, Brian A
Tucker, James K
Moebius, David C
Shair, Matthew D
description A general strategy for the synthesis of polycyclic polyprenylated acylphloroglucinols is described in which a scalable, Lewis acid catalyzed epoxide-opening cascade cyclization is used to furnish common intermediate 4. The utility of this approach is exemplified by the total syntheses of both ent-nemorosone and (+)-secohyperforin, which were each accomplished in four steps from this intermediate.
doi_str_mv 10.1021/acs.orglett.5b01121
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subjects Benzophenones - chemical synthesis
Benzophenones - chemistry
Cyclization
Epoxy Compounds - chemistry
Lewis Acids - chemistry
Molecular Structure
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemical synthesis
Phloroglucinol - chemistry
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
title Total Synthesis of (−)-Nemorosone and (+)-Secohyperforin
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