A concise and enantioselective approach to the total synthesis of (-)-lasubine I

Shengyang Liu; Yuping Fan; Xinxiang Peng; Wei Wang; Weiyi Hua; Haji Akber; Lixin Liao

doi:10.1016/j.tetlet.2006.08.137

A concise and enantioselective approach to the total synthesis of (-)-lasubine I

Shengyang Liu, Yuping Fan, Xinxiang Peng, Wei Wang, Weiyi Hua, Haji Akber, Lixin Liao

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

28 Scopus citations

Abstract

An efficient, enantioselective total synthesis of (-)-lasubine I (1) has been achieved in an overall 8.8% yield from readily available starting materials. The important features of this approach include the creation of stereogenic centers through two sequential highly stereoselective Roush allylborations and the use of S_N2 cyclization and ring-closing metathesis reactions for the construction of the quinolizidine skeleton.

Original language	English (US)
Pages (from-to)	7681-7684
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2006.08.137
State	Published - Oct 30 2006
Externally published	Yes

Keywords

Lasubine
Quinolizidine
Ring-closing metathesis
Roush allylboration

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2006.08.137

Cite this

@article{55ad6894f6824fb18c9a95a4a86d0bb6,

title = "A concise and enantioselective approach to the total synthesis of (-)-lasubine I",

abstract = "An efficient, enantioselective total synthesis of (-)-lasubine I (1) has been achieved in an overall 8.8% yield from readily available starting materials. The important features of this approach include the creation of stereogenic centers through two sequential highly stereoselective Roush allylborations and the use of SN2 cyclization and ring-closing metathesis reactions for the construction of the quinolizidine skeleton.",

keywords = "Lasubine, Quinolizidine, Ring-closing metathesis, Roush allylboration",

author = "Shengyang Liu and Yuping Fan and Xinxiang Peng and Wei Wang and Weiyi Hua and Haji Akber and Lixin Liao",

note = "Funding Information: We are grateful for the financial support from the National Natural Science Foundation of China (No. 20372082, L.-X.L.) and the Department of Medicinal Chemistry, School of Pharmacy, East China University of Science and Technology (W.W.). ",

year = "2006",

month = oct,

day = "30",

doi = "10.1016/j.tetlet.2006.08.137",

language = "English (US)",

volume = "47",

pages = "7681--7684",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "44",

}

TY - JOUR

T1 - A concise and enantioselective approach to the total synthesis of (-)-lasubine I

AU - Liu, Shengyang

AU - Fan, Yuping

AU - Peng, Xinxiang

AU - Wang, Wei

AU - Hua, Weiyi

AU - Akber, Haji

AU - Liao, Lixin

N1 - Funding Information: We are grateful for the financial support from the National Natural Science Foundation of China (No. 20372082, L.-X.L.) and the Department of Medicinal Chemistry, School of Pharmacy, East China University of Science and Technology (W.W.).

PY - 2006/10/30

Y1 - 2006/10/30

N2 - An efficient, enantioselective total synthesis of (-)-lasubine I (1) has been achieved in an overall 8.8% yield from readily available starting materials. The important features of this approach include the creation of stereogenic centers through two sequential highly stereoselective Roush allylborations and the use of SN2 cyclization and ring-closing metathesis reactions for the construction of the quinolizidine skeleton.

AB - An efficient, enantioselective total synthesis of (-)-lasubine I (1) has been achieved in an overall 8.8% yield from readily available starting materials. The important features of this approach include the creation of stereogenic centers through two sequential highly stereoselective Roush allylborations and the use of SN2 cyclization and ring-closing metathesis reactions for the construction of the quinolizidine skeleton.

KW - Lasubine

KW - Quinolizidine

KW - Ring-closing metathesis

KW - Roush allylboration

UR - http://www.scopus.com/inward/record.url?scp=33749128100&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33749128100&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.08.137

DO - 10.1016/j.tetlet.2006.08.137

M3 - Article

AN - SCOPUS:33749128100

SN - 0040-4039

VL - 47

SP - 7681

EP - 7684

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

A concise and enantioselective approach to the total synthesis of (-)-lasubine I

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this