Enantioselective Total Synthesis of RQN-18690A (18-Deoxyherboxidiene)

Yasunobu Matsumoto; Kazuhiro Hibino; Masahiro Yonaga; Hideaki Kakeya; Yujiro Hayashi

doi:10.1021/acs.orglett.6b01524

Enantioselective Total Synthesis of RQN-18690A (18-Deoxyherboxidiene)

Yasunobu Matsumoto, Kazuhiro Hibino, Masahiro Yonaga, Hideaki Kakeya, Yujiro Hayashi

SCI - Chemistry

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

8 Citations (Scopus)

Abstract

The first total synthesis of RQN-18690A (18-deoxyherboxidiene) and the determination of its absolute stereochemical configuration are described. The synthesis features an organocatalytic aldol reaction for the first step, 1,4- and 1,2- dual reductions of α,β-unsaturated δ-lactone followed by a domino reaction in a one-pot operation, and diastereoselective epoxidation with kinetic resolution.

Original language	English
Pages (from-to)	3382-3385
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.6b01524
Publication status	Published - 2016 Jul 15

Access to Document

10.1021/acs.orglett.6b01524

Cite this

@article{b081a4ecb58a45aabd0663b24bd35360,

title = "Enantioselective Total Synthesis of RQN-18690A (18-Deoxyherboxidiene)",

abstract = "The first total synthesis of RQN-18690A (18-deoxyherboxidiene) and the determination of its absolute stereochemical configuration are described. The synthesis features an organocatalytic aldol reaction for the first step, 1,4- and 1,2- dual reductions of α,β-unsaturated δ-lactone followed by a domino reaction in a one-pot operation, and diastereoselective epoxidation with kinetic resolution.",

author = "Yasunobu Matsumoto and Kazuhiro Hibino and Masahiro Yonaga and Hideaki Kakeya and Yujiro Hayashi",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = jul,

day = "15",

doi = "10.1021/acs.orglett.6b01524",

language = "English",

volume = "18",

pages = "3382--3385",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Enantioselective Total Synthesis of RQN-18690A (18-Deoxyherboxidiene)

AU - Matsumoto, Yasunobu

AU - Hibino, Kazuhiro

AU - Yonaga, Masahiro

AU - Kakeya, Hideaki

AU - Hayashi, Yujiro

PY - 2016/7/15

Y1 - 2016/7/15

N2 - The first total synthesis of RQN-18690A (18-deoxyherboxidiene) and the determination of its absolute stereochemical configuration are described. The synthesis features an organocatalytic aldol reaction for the first step, 1,4- and 1,2- dual reductions of α,β-unsaturated δ-lactone followed by a domino reaction in a one-pot operation, and diastereoselective epoxidation with kinetic resolution.

AB - The first total synthesis of RQN-18690A (18-deoxyherboxidiene) and the determination of its absolute stereochemical configuration are described. The synthesis features an organocatalytic aldol reaction for the first step, 1,4- and 1,2- dual reductions of α,β-unsaturated δ-lactone followed by a domino reaction in a one-pot operation, and diastereoselective epoxidation with kinetic resolution.

UR - http://www.scopus.com/inward/record.url?scp=84978630913&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84978630913&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b01524

DO - 10.1021/acs.orglett.6b01524

M3 - Article

AN - SCOPUS:84978630913

SN - 1523-7060

VL - 18

SP - 3382

EP - 3385

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Enantioselective Total Synthesis of RQN-18690A (18-Deoxyherboxidiene)

Abstract

Access to Document

Other files and links

Fingerprint

Cite this