A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine

Kevin I. Booker-Milburn; Paul Hirst; Jonathan P H Charmant; Luke H J Taylor

doi:10.1002/anie.200250507

A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine

Kevin I. Booker-Milburn^*, Paul Hirst, Jonathan P H Charmant, Luke H J Taylor

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

29 Citations (Scopus)

Abstract

Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated S_N2′ ring-opening desymmetrization of the C₂-symmetric bislactone 4.

Translated title of the contribution	A Rapid Stereocontrolled Entry to the ABCD Tetracyclic Core of Neotuberostemonine
Original language	English
Pages (from-to)	1642-1644
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	14
DOIs	https://doi.org/10.1002/anie.200250507
Publication status	Published - 11 Apr 2003

Bibliographical note

Publisher: Wiley

Keywords

Asymmetric synthesis
Cuprates
Lactones
Natural products
Photocyclization
Total synthesis

Access to Document

10.1002/anie.200250507

http://www3.interscience.wiley.com/cgi-bin/abstract/104524479/ABSTRACT

Handle.net

Persistent link

Cite this

@article{e224c47f792e4bcf9a3df871ea30934b,

title = "A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine",

abstract = "Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4.",

keywords = "Asymmetric synthesis, Cuprates, Lactones, Natural products, Photocyclization, Total synthesis",

author = "Booker-Milburn, {Kevin I.} and Paul Hirst and Charmant, {Jonathan P H} and Taylor, {Luke H J}",

note = "Publisher: Wiley",

year = "2003",

month = apr,

day = "11",

doi = "10.1002/anie.200250507",

language = "English",

volume = "42",

pages = "1642--1644",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "14",

}

TY - JOUR

T1 - A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine

AU - Booker-Milburn, Kevin I.

AU - Hirst, Paul

AU - Charmant, Jonathan P H

AU - Taylor, Luke H J

N1 - Publisher: Wiley

PY - 2003/4/11

Y1 - 2003/4/11

N2 - Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4.

AB - Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4.

KW - Asymmetric synthesis

KW - Cuprates

KW - Lactones

KW - Natural products

KW - Photocyclization

KW - Total synthesis

U2 - 10.1002/anie.200250507

DO - 10.1002/anie.200250507

M3 - Article (Academic Journal)

C2 - 12698465

VL - 42

SP - 1642

EP - 1644

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 14

ER -

A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine

Abstract

Bibliographical note

Keywords

Access to Document

Handle.net

Fingerprint

Cite this