A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis

Yinan Zhang; Xiachang Wang; Manjula Sunkara; Qing Ye; Larissa V. Ponomereva; Qing Bai She; Andrew J. Morris; Jon S. Thorson

doi:10.1021/ol4027649

A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis

Yinan Zhang, Xiachang Wang, Manjula Sunkara, Qing Ye, Larissa V. Ponomereva, Qing Bai She, Andrew J. Morris, Jon S. Thorson

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

Original language	English
Pages (from-to)	5566-5569
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	21
DOIs	https://doi.org/10.1021/ol4027649
State	Published - Nov 1 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis",

abstract = "An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.",

author = "Yinan Zhang and Xiachang Wang and Manjula Sunkara and Qing Ye and Ponomereva, {Larissa V.} and She, {Qing Bai} and Morris, {Andrew J.} and Thorson, {Jon S.}",

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T1 - A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis

AU - Zhang, Yinan

AU - Wang, Xiachang

AU - Sunkara, Manjula

AU - Ye, Qing

AU - Ponomereva, Larissa V.

AU - She, Qing Bai

AU - Morris, Andrew J.

AU - Thorson, Jon S.

PY - 2013/11/1

Y1 - 2013/11/1

N2 - An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

AB - An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

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A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis

Abstract

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