A short synthesis of the C15-C21 segment of (+)-discodermolide, based on an asymmetric approach from achiral 2-methyl-1,3-propanediol to versatile enantiopure stereotriads

Shahid Abdus Kazi; Yong Nan Li; Momotoshi Okazaki; Yoshihiro Shuto; Fumitaka Goto; Syun-ichi Kiyooka

A short synthesis of the C15-C21 segment of (+)-discodermolide, based on an asymmetric approach from achiral 2-methyl-1,3-propanediol to versatile enantiopure stereotriads

Shahid Abdus Kazi, Yong Nan Li, Momotoshi Okazaki, Yoshihiro Shuto, Fumitaka Goto, Syun-ichi Kiyooka

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

Abstract

A new approach was developed to versatile enantiopure stereotriads using chiral oxazaborolidinone-promoted asym. aldol reaction of a racemic aldehyde with a bromo silyl nucleophile. A short synthesis of the C15-C21 segment I of (+)-discodermolide was achieved by elongation of one of the stereotriads with further diastereoselective aldol reaction with the same nucleophile. [on SciFinder(R)]

Original language	English
Pages (from-to)	6373 - 6376
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	36
Publication status	Published - 2002
Externally published	Yes

Cite this

@article{76a7ee816e374fd89a4b333e46470c51,

title = "A short synthesis of the C15-C21 segment of (+)-discodermolide, based on an asymmetric approach from achiral 2-methyl-1,3-propanediol to versatile enantiopure stereotriads",

abstract = "A new approach was developed to versatile enantiopure stereotriads using chiral oxazaborolidinone-promoted asym. aldol reaction of a racemic aldehyde with a bromo silyl nucleophile. A short synthesis of the C15-C21 segment I of (+)-discodermolide was achieved by elongation of one of the stereotriads with further diastereoselective aldol reaction with the same nucleophile. [on SciFinder(R)]",

author = "Kazi, {Shahid Abdus} and Li, {Yong Nan} and Momotoshi Okazaki and Yoshihiro Shuto and Fumitaka Goto and Syun-ichi Kiyooka",

year = "2002",

language = "English",

volume = "43",

pages = "6373 -- 6376",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "36",

}

A short synthesis of the C15-C21 segment of (+)-discodermolide, based on an asymmetric approach from achiral 2-methyl-1,3-propanediol to versatile enantiopure stereotriads. / Kazi, Shahid Abdus; Li, Yong Nan; Okazaki, Momotoshi et al.
In: Tetrahedron Letters, Vol. 43, No. 36, 2002, p. 6373 - 6376.

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

TY - JOUR

T1 - A short synthesis of the C15-C21 segment of (+)-discodermolide, based on an asymmetric approach from achiral 2-methyl-1,3-propanediol to versatile enantiopure stereotriads

AU - Kazi, Shahid Abdus

AU - Li, Yong Nan

AU - Okazaki, Momotoshi

AU - Shuto, Yoshihiro

AU - Goto, Fumitaka

AU - Kiyooka, Syun-ichi

PY - 2002

Y1 - 2002

N2 - A new approach was developed to versatile enantiopure stereotriads using chiral oxazaborolidinone-promoted asym. aldol reaction of a racemic aldehyde with a bromo silyl nucleophile. A short synthesis of the C15-C21 segment I of (+)-discodermolide was achieved by elongation of one of the stereotriads with further diastereoselective aldol reaction with the same nucleophile. [on SciFinder(R)]

AB - A new approach was developed to versatile enantiopure stereotriads using chiral oxazaborolidinone-promoted asym. aldol reaction of a racemic aldehyde with a bromo silyl nucleophile. A short synthesis of the C15-C21 segment I of (+)-discodermolide was achieved by elongation of one of the stereotriads with further diastereoselective aldol reaction with the same nucleophile. [on SciFinder(R)]

M3 - Article

SN - 0040-4039

VL - 43

SP - 6373

EP - 6376

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -