Enantioselective synthesis of a 3'-dephenylcryptophycin synthon

Mari Jean Eggen; Gunda I. Georg

doi:10.1016/S0960-894X(98)00557-5

Enantioselective synthesis of a 3'-dephenylcryptophycin synthon

Mari Jean Eggen, Gunda I. Georg

Medicinal Chemistry

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

17 Scopus citations

Abstract

An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert- butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.

Original language	English (US)
Pages (from-to)	3177-3180
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	8
Issue number	22
DOIs	https://doi.org/10.1016/S0960-894X(98)00557-5
State	Published - Nov 17 1998

Access

10.1016/S0960-894X(98)00557-5

OpenUrl availability

Full text

Cite this

@article{12a15a9758a64215b315d1de047d0b0d,

title = "Enantioselective synthesis of a 3'-dephenylcryptophycin synthon",

abstract = "An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert- butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.",

author = "Eggen, {Mari Jean} and Georg, {Gunda I.}",

year = "1998",

month = nov,

day = "17",

doi = "10.1016/S0960-894X(98)00557-5",

language = "English (US)",

volume = "8",

pages = "3177--3180",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "22",

}

TY - JOUR

T1 - Enantioselective synthesis of a 3'-dephenylcryptophycin synthon

AU - Eggen, Mari Jean

AU - Georg, Gunda I.

PY - 1998/11/17

Y1 - 1998/11/17

N2 - An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert- butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.

AB - An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert- butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.

UR - http://www.scopus.com/inward/record.url?scp=0032542038&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032542038&partnerID=8YFLogxK

U2 - 10.1016/S0960-894X(98)00557-5

DO - 10.1016/S0960-894X(98)00557-5

M3 - Article

C2 - 9873698

AN - SCOPUS:0032542038

SN - 0960-894X

VL - 8

SP - 3177

EP - 3180

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 22

ER -

Enantioselective synthesis of a 3'-dephenylcryptophycin synthon

Abstract

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this