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

^*Corresponding author for this work

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

37 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4271-4274
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(00)73331-4
Publication status	Published - 1994 Jun 20
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)73331-4

Cite this

@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 - https://www.scopus.com/pages/publications/0028338336

UR - https://www.scopus.com/pages/publications/0028338336#tab=citedBy

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this