Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction

Shin Ichi Shirokawa; Mariko Shinoyama; Isao Ooi; Seijiro Hosokawa; Atsuo Nakazaki; Susumu Kobayashi

doi:10.1021/ol0630191

Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction

Shin Ichi Shirokawa, Mariko Shinoyama, Isao Ooi, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi^*

^*Corresponding author for this work

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

49 Citations (Scopus)

Abstract

(Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl ₄-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.

Original language	English
Pages (from-to)	849-852
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/ol0630191
Publication status	Published - 2007 Mar 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol0630191

Cite this

@article{dd0c74dd5dd24c16b9aa1d60be95c0c0,

title = "Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction",

abstract = "(Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.",

author = "Shirokawa, {Shin Ichi} and Mariko Shinoyama and Isao Ooi and Seijiro Hosokawa and Atsuo Nakazaki and Susumu Kobayashi",

year = "2007",

month = mar,

day = "1",

doi = "10.1021/ol0630191",

language = "English",

volume = "9",

pages = "849--852",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction

AU - Shirokawa, Shin Ichi

AU - Shinoyama, Mariko

AU - Ooi, Isao

AU - Hosokawa, Seijiro

AU - Nakazaki, Atsuo

AU - Kobayashi, Susumu

PY - 2007/3/1

Y1 - 2007/3/1

N2 - (Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.

AB - (Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.

UR - http://www.scopus.com/inward/record.url?scp=33947118711&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947118711&partnerID=8YFLogxK

U2 - 10.1021/ol0630191

DO - 10.1021/ol0630191

M3 - Article

C2 - 17288429

AN - SCOPUS:33947118711

SN - 1523-7060

VL - 9

SP - 849

EP - 852

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this