Stereoselective total synthesis of (-)-batzellasides a, b, and c

Toru Okaki; Ryohei Fujimura; Masataka Sekiguchi; Dejun Zhou; Kenji Sugimoto; Daishiro Minato; Yuji Matsuya; Atsushi Kato; Isao Adachi; Yasuhiro Tezuka; Ralph A. Saporito; Naoki Toyooka

doi:10.1002/ejoc.201201567

Stereoselective total synthesis of (-)-batzellasides a, b, and c

Toru Okaki, Ryohei Fujimura, Masataka Sekiguchi, Dejun Zhou, Kenji Sugimoto, Daishiro Minato, Yuji Matsuya, Atsushi Kato, Isao Adachi, Yasuhiro Tezuka, Ralph A. Saporito, Naoki Toyooka^*

^*Corresponding author for this work

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

6 Scopus citations

Abstract

Total synthesis of (-)-L-batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1 position by acyliminium chemistry and Brown's asymmetric allylation of the corresponding aldehydes to construct a stereocenter on the side chain.

Original language	English
Pages (from-to)	2841-2848
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	14
DOIs	https://doi.org/10.1002/ejoc.201201567
State	Published - 2013/05

Keywords

Allylation
Asymmetric synthesis
Natural products
Nitrogen heterocycles
Total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201201567

Cite this

@article{ec0550e66bdf46138f783019a3a59aca,

title = "Stereoselective total synthesis of (-)-batzellasides a, b, and c",

abstract = "Total synthesis of (-)-L-batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1 position by acyliminium chemistry and Brown's asymmetric allylation of the corresponding aldehydes to construct a stereocenter on the side chain.",

keywords = "Allylation, Asymmetric synthesis, Natural products, Nitrogen heterocycles, Total synthesis",

author = "Toru Okaki and Ryohei Fujimura and Masataka Sekiguchi and Dejun Zhou and Kenji Sugimoto and Daishiro Minato and Yuji Matsuya and Atsushi Kato and Isao Adachi and Yasuhiro Tezuka and Saporito, {Ralph A.} and Naoki Toyooka",

year = "2013",

month = may,

doi = "10.1002/ejoc.201201567",

language = "英語",

pages = "2841--2848",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "14",

}

TY - JOUR

T1 - Stereoselective total synthesis of (-)-batzellasides a, b, and c

AU - Okaki, Toru

AU - Fujimura, Ryohei

AU - Sekiguchi, Masataka

AU - Zhou, Dejun

AU - Sugimoto, Kenji

AU - Minato, Daishiro

AU - Matsuya, Yuji

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Tezuka, Yasuhiro

AU - Saporito, Ralph A.

AU - Toyooka, Naoki

PY - 2013/5

Y1 - 2013/5

N2 - Total synthesis of (-)-L-batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1 position by acyliminium chemistry and Brown's asymmetric allylation of the corresponding aldehydes to construct a stereocenter on the side chain.

AB - Total synthesis of (-)-L-batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1 position by acyliminium chemistry and Brown's asymmetric allylation of the corresponding aldehydes to construct a stereocenter on the side chain.

KW - Allylation

KW - Asymmetric synthesis

KW - Natural products

KW - Nitrogen heterocycles

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84877689408&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201201567

DO - 10.1002/ejoc.201201567

M3 - 学術論文

AN - SCOPUS:84877689408

SN - 1434-193X

SP - 2841

EP - 2848

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 14

ER -

Stereoselective total synthesis of (-)-batzellasides a, b, and c

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this