Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction

Hiroaki Matoba; Takahiro Watanabe; Masanori Nagatomo; Masayuki Inoue

doi:10.1021/acs.orglett.8b03302

Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction

Hiroaki Matoba, Takahiro Watanabe, Masanori Nagatomo, Masayuki Inoue

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

7 Citations (Scopus)

Abstract

The highly oxygenated 6/8/6-membered ABC-ring 2 of taxol was assembled in a convergent fashion. A decarbonylative radical reaction between α-alkoxyacyl telluride 4 and cyanocyclohexenone 5 linked the A- and C-rings and stereoselectively installed the C2- and C3-tertiary carbon centers of 3. After the C8-quaternary stereocenter was constructed, the C9-methyl ketone and the C11-vinyl triflate of 30 participated in Pd(0)-promoted cyclization of the eight-membered B-ring, giving rise to the taxol skeleton 2.

Original language	English
Pages (from-to)	7554-7557
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.8b03302
Publication status	Published - 2018 Dec 7
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b03302

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title = "Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction",

abstract = "The highly oxygenated 6/8/6-membered ABC-ring 2 of taxol was assembled in a convergent fashion. A decarbonylative radical reaction between α-alkoxyacyl telluride 4 and cyanocyclohexenone 5 linked the A- and C-rings and stereoselectively installed the C2- and C3-tertiary carbon centers of 3. After the C8-quaternary stereocenter was constructed, the C9-methyl ketone and the C11-vinyl triflate of 30 participated in Pd(0)-promoted cyclization of the eight-membered B-ring, giving rise to the taxol skeleton 2.",

author = "Hiroaki Matoba and Takahiro Watanabe and Masanori Nagatomo and Masayuki Inoue",

note = "Funding Information: This research was financially supported by Grants-in-Aid for Scientific Research (S) (17H06110) for Scientific Research on Innovative Areas (17H06452) to M.I. and Grants-in-Aid for Scientific Research (C) (16K08156) for Scientific Research on Innovative Areas (18H04384) to M.N. from JSPS. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = dec,

day = "7",

doi = "10.1021/acs.orglett.8b03302",

language = "English",

volume = "20",

pages = "7554--7557",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

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T1 - Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction

AU - Matoba, Hiroaki

AU - Watanabe, Takahiro

AU - Nagatomo, Masanori

AU - Inoue, Masayuki

N1 - Funding Information: This research was financially supported by Grants-in-Aid for Scientific Research (S) (17H06110) for Scientific Research on Innovative Areas (17H06452) to M.I. and Grants-in-Aid for Scientific Research (C) (16K08156) for Scientific Research on Innovative Areas (18H04384) to M.N. from JSPS. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/12/7

Y1 - 2018/12/7

N2 - The highly oxygenated 6/8/6-membered ABC-ring 2 of taxol was assembled in a convergent fashion. A decarbonylative radical reaction between α-alkoxyacyl telluride 4 and cyanocyclohexenone 5 linked the A- and C-rings and stereoselectively installed the C2- and C3-tertiary carbon centers of 3. After the C8-quaternary stereocenter was constructed, the C9-methyl ketone and the C11-vinyl triflate of 30 participated in Pd(0)-promoted cyclization of the eight-membered B-ring, giving rise to the taxol skeleton 2.

AB - The highly oxygenated 6/8/6-membered ABC-ring 2 of taxol was assembled in a convergent fashion. A decarbonylative radical reaction between α-alkoxyacyl telluride 4 and cyanocyclohexenone 5 linked the A- and C-rings and stereoselectively installed the C2- and C3-tertiary carbon centers of 3. After the C8-quaternary stereocenter was constructed, the C9-methyl ketone and the C11-vinyl triflate of 30 participated in Pd(0)-promoted cyclization of the eight-membered B-ring, giving rise to the taxol skeleton 2.

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DO - 10.1021/acs.orglett.8b03302

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 23

ER -

Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction

Abstract

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