Total Synthesis of (-)-Xestosaprol N and O

Yingbo Shi; Yang Ji; Kunyun Xin; Shuanhu Gao

doi:10.1021/acs.orglett.7b03865

Total Synthesis of (-)-Xestosaprol N and O

Yingbo Shi, Yang Ji, Kunyun Xin, Shuanhu Gao

School of Chemistry and Molecular Engineering

East China Normal University

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

16 Scopus citations

Abstract

The first total synthesis of (-)-xestosaprol N and O is described. This synthetic work features a convergent strategy: (1) a Pd-catalyzed arylation followed by cyclization to build a naphthalene fragment (ring C, D); (2) utilization of (-)-quinic acid to construct the chiral hydroxyl group at C-2; (3) a substrate controlled intramolecular Heck reaction to construct a quaternary carbon center (ring B); (4) introduction of a hypotaurine moiety at a late stage to furnish the E ring.

Original language	English
Pages (from-to)	732-735
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.7b03865
State	Published - 2 Feb 2018

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abstract = "The first total synthesis of (-)-xestosaprol N and O is described. This synthetic work features a convergent strategy: (1) a Pd-catalyzed arylation followed by cyclization to build a naphthalene fragment (ring C, D); (2) utilization of (-)-quinic acid to construct the chiral hydroxyl group at C-2; (3) a substrate controlled intramolecular Heck reaction to construct a quaternary carbon center (ring B); (4) introduction of a hypotaurine moiety at a late stage to furnish the E ring.",

author = "Yingbo Shi and Yang Ji and Kunyun Xin and Shuanhu Gao",

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AU - Ji, Yang

AU - Xin, Kunyun

AU - Gao, Shuanhu

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AB - The first total synthesis of (-)-xestosaprol N and O is described. This synthetic work features a convergent strategy: (1) a Pd-catalyzed arylation followed by cyclization to build a naphthalene fragment (ring C, D); (2) utilization of (-)-quinic acid to construct the chiral hydroxyl group at C-2; (3) a substrate controlled intramolecular Heck reaction to construct a quaternary carbon center (ring B); (4) introduction of a hypotaurine moiety at a late stage to furnish the E ring.

UR - https://www.scopus.com/pages/publications/85041612569

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DO - 10.1021/acs.orglett.7b03865

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SP - 732

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JO - Organic Letters

JF - Organic Letters

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ER -

Total Synthesis of (-)-Xestosaprol N and O

Abstract

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