Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic

Amos B. Smith; Kwunmin Chen; Darius J. Robinson; Leif M. Laakso; Karl J. Hale

doi:10.1016/S0040-4039(00)73331-4

Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic

Amos B. Smith^*, Kwunmin Chen, Darius J. Robinson, Leif M. Laakso, Karl J. Hale

^*此作品的通信作者

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

35 引文斯高帕斯（Scopus）

摘要

A formal total synthesis of the potent immunosuppressant FK506 (1) has been achieved via a concise construction of the Merck advanced intermediate (-)-2. Key features of the successful strategy include stereocontrolled σ-bond installation of the trisubstituted olefin moieties and an efficient coupling of the C(24)-C(34) dithiane (-)-10 with the C(10)-C(23) α-silyloxy primary iodide (-)-9.

原文	英語
頁（從 - 到）	4271-4274
頁數	4
期刊	Tetrahedron Letters
卷	35
發行號	25
DOIs	https://doi.org/10.1016/S0040-4039(00)73331-4
出版狀態	已發佈 - 1994 6月 20
對外發佈	是

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/S0040-4039(00)73331-4

其它文件與鏈接

引用此

@article{ff1f5d05fcea44519b9b22a29f382182,

title = "Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic",

abstract = "A formal total synthesis of the potent immunosuppressant FK506 (1) has been achieved via a concise construction of the Merck advanced intermediate (-)-2. Key features of the successful strategy include stereocontrolled σ-bond installation of the trisubstituted olefin moieties and an efficient coupling of the C(24)-C(34) dithiane (-)-10 with the C(10)-C(23) α-silyloxy primary iodide (-)-9.",

author = "Smith, {Amos B.} and Kwunmin Chen and Robinson, {Darius J.} and Laakso, {Leif M.} and Hale, {Karl J.}",

year = "1994",

month = jun,

day = "20",

doi = "10.1016/S0040-4039(00)73331-4",

language = "English",

volume = "35",

pages = "4271--4274",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "25",

}

TY - JOUR

T1 - Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic

AU - Smith, Amos B.

AU - Chen, Kwunmin

AU - Robinson, Darius J.

AU - Laakso, Leif M.

AU - Hale, Karl J.

PY - 1994/6/20

Y1 - 1994/6/20

N2 - A formal total synthesis of the potent immunosuppressant FK506 (1) has been achieved via a concise construction of the Merck advanced intermediate (-)-2. Key features of the successful strategy include stereocontrolled σ-bond installation of the trisubstituted olefin moieties and an efficient coupling of the C(24)-C(34) dithiane (-)-10 with the C(10)-C(23) α-silyloxy primary iodide (-)-9.

AB - A formal total synthesis of the potent immunosuppressant FK506 (1) has been achieved via a concise construction of the Merck advanced intermediate (-)-2. Key features of the successful strategy include stereocontrolled σ-bond installation of the trisubstituted olefin moieties and an efficient coupling of the C(24)-C(34) dithiane (-)-10 with the C(10)-C(23) α-silyloxy primary iodide (-)-9.

UR - http://www.scopus.com/inward/record.url?scp=0028338336&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028338336&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)73331-4

DO - 10.1016/S0040-4039(00)73331-4

M3 - Article

AN - SCOPUS:0028338336

SN - 0040-4039

VL - 35

SP - 4271

EP - 4274

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

引用此