Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

Shao Chien Hsu; Mogili Narsingam; Yi Fang Lin; Feng Lin Hsu; Biing Jiun Uang

doi:10.1016/j.tet.2013.01.055

Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

Shao Chien Hsu
, Mogili Narsingam
, Yi Fang Lin
, Feng Lin Hsu
, Biing Jiun Uang

School of Pharmacy

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

13 Citations (Scopus)

Abstract

A practical synthesis of (±)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.

Original language	English
Pages (from-to)	2572-2576
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2013.01.055
Publication status	Published - Mar 25 2013

Keywords

Potassium vinyltrifluoroborate
Pterosin A
Suzuki-Miyaura reaction
Vinylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.01.055

Cite this

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title = "Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction",

abstract = "A practical synthesis of (±)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10\% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85\% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.",

keywords = "Potassium vinyltrifluoroborate, Pterosin A, Suzuki-Miyaura reaction, Vinylation",

author = "Hsu, \{Shao Chien\} and Mogili Narsingam and Lin, \{Yi Fang\} and Hsu, \{Feng Lin\} and Uang, \{Biing Jiun\}",

year = "2013",

month = mar,

day = "25",

doi = "10.1016/j.tet.2013.01.055",

language = "English",

volume = "69",

pages = "2572--2576",

journal = "Tetrahedron",

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number = "12",

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TY - JOUR

T1 - Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

AU - Hsu, Shao Chien

AU - Narsingam, Mogili

AU - Lin, Yi Fang

AU - Hsu, Feng Lin

AU - Uang, Biing Jiun

PY - 2013/3/25

Y1 - 2013/3/25

N2 - A practical synthesis of (±)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.

AB - A practical synthesis of (±)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.

KW - Potassium vinyltrifluoroborate

KW - Pterosin A

KW - Suzuki-Miyaura reaction

KW - Vinylation

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UR - https://www.scopus.com/pages/publications/84874113414#tab=citedBy

U2 - 10.1016/j.tet.2013.01.055

DO - 10.1016/j.tet.2013.01.055

M3 - Article

AN - SCOPUS:84874113414

SN - 0040-4020

VL - 69

SP - 2572

EP - 2576

JO - Tetrahedron

JF - Tetrahedron

IS - 12

ER -

Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

Abstract

Keywords

ASJC Scopus subject areas

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