Synthesis of the ABC ring system of paclitaxel: Formation of the 8-membered B ring by intramolecular alkylation

S. Miyamoto; T. Doi; T. Takahashi

doi:10.1055/s-2002-19359

Synthesis of the ABC ring system of paclitaxel: Formation of the 8-membered B ring by intramolecular alkylation

S. Miyamoto, T. Doi, T. Takahashi

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

11 Citations (Scopus)

Abstract

The formation of the B ring of the ABC ring system of paclitaxel was accomplished by intramolecular alkylation of the protected cyanohydrin ether in the presence of the 7-alkoxy group on the C ring. A significant effect of the protective groups at the 1,2-positions was observed in this alkylation. Acyclic protection provided the desired compound 3c and 3d in moderate yields, whereas cyclic protection led to 3a in low yield.

Original language	English
Pages (from-to)	97-99
Number of pages	3
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2002-19359
Publication status	Published - 2002 Jan 1
Externally published	Yes

Keywords

Cyanohydrins
Intramolecular alkylations
Paclitaxel
Terpenoids

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-2002-19359

Fingerprint Dive into the research topics of 'Synthesis of the ABC ring system of paclitaxel: Formation of the 8-membered B ring by intramolecular alkylation'. Together they form a unique fingerprint.

Cite this

@article{61cd8cbbae004fbd935e32e2dc94f9d0,

title = "Synthesis of the ABC ring system of paclitaxel: Formation of the 8-membered B ring by intramolecular alkylation",

abstract = "The formation of the B ring of the ABC ring system of paclitaxel was accomplished by intramolecular alkylation of the protected cyanohydrin ether in the presence of the 7-alkoxy group on the C ring. A significant effect of the protective groups at the 1,2-positions was observed in this alkylation. Acyclic protection provided the desired compound 3c and 3d in moderate yields, whereas cyclic protection led to 3a in low yield.",

keywords = "Cyanohydrins, Intramolecular alkylations, Paclitaxel, Terpenoids",

author = "S. Miyamoto and T. Doi and T. Takahashi",

year = "2002",

month = jan,

day = "1",

doi = "10.1055/s-2002-19359",

language = "English",

pages = "97--99",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - Synthesis of the ABC ring system of paclitaxel

T2 - Formation of the 8-membered B ring by intramolecular alkylation

AU - Miyamoto, S.

AU - Doi, T.

AU - Takahashi, T.

PY - 2002/1/1

Y1 - 2002/1/1

N2 - The formation of the B ring of the ABC ring system of paclitaxel was accomplished by intramolecular alkylation of the protected cyanohydrin ether in the presence of the 7-alkoxy group on the C ring. A significant effect of the protective groups at the 1,2-positions was observed in this alkylation. Acyclic protection provided the desired compound 3c and 3d in moderate yields, whereas cyclic protection led to 3a in low yield.

AB - The formation of the B ring of the ABC ring system of paclitaxel was accomplished by intramolecular alkylation of the protected cyanohydrin ether in the presence of the 7-alkoxy group on the C ring. A significant effect of the protective groups at the 1,2-positions was observed in this alkylation. Acyclic protection provided the desired compound 3c and 3d in moderate yields, whereas cyclic protection led to 3a in low yield.

KW - Cyanohydrins

KW - Intramolecular alkylations

KW - Paclitaxel

KW - Terpenoids

UR - http://www.scopus.com/inward/record.url?scp=0036139947&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036139947&partnerID=8YFLogxK

U2 - 10.1055/s-2002-19359

DO - 10.1055/s-2002-19359

M3 - Article

AN - SCOPUS:0036139947

SP - 97

EP - 99

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 1

ER -