The University of Southampton
University of Southampton Institutional Repository

Total synthesis of cis-sylvaticin

Total synthesis of cis-sylvaticin
Total synthesis of cis-sylvaticin
An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.
antitumor, enantioselective total-synthesis, oxidative cyclization, (+)-gigantecin, allylic alcohols, mucocin, (-)-mucocin, metathesis approach, recent progress, agent, annonaceous acetogenins
1523-7060
2489-2492
Brown, L.J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Spurr, I.B.
f5eafa64-17a6-4f9b-b979-96d32a02197c
Kemp, S.C.
90bfffca-b4a8-48a4-b732-f6e709d4819b
Camp, N.P.
6976e25d-ca23-4013-85dd-f7eb1ac5f612
Gibson, K.R.
65e9d4d0-64bd-4cb7-aefc-14ee35337e65
Brown, R.C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Brown, L.J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Spurr, I.B.
f5eafa64-17a6-4f9b-b979-96d32a02197c
Kemp, S.C.
90bfffca-b4a8-48a4-b732-f6e709d4819b
Camp, N.P.
6976e25d-ca23-4013-85dd-f7eb1ac5f612
Gibson, K.R.
65e9d4d0-64bd-4cb7-aefc-14ee35337e65
Brown, R.C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Brown, L.J., Spurr, I.B., Kemp, S.C., Camp, N.P., Gibson, K.R. and Brown, R.C.D. (2008) Total synthesis of cis-sylvaticin. Organic Letters, 10 (12), 2489-2492. (doi:10.1021/ol800767e).

Record type: Article

Abstract

An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.

Full text not available from this repository.

More information

e-pub ahead of print date: 20 May 2008
Published date: 19 June 2008
Keywords: antitumor, enantioselective total-synthesis, oxidative cyclization, (+)-gigantecin, allylic alcohols, mucocin, (-)-mucocin, metathesis approach, recent progress, agent, annonaceous acetogenins
Organisations: Chemistry

Identifiers

Local EPrints ID: 54430
URI: https://eprints.soton.ac.uk/id/eprint/54430
ISSN: 1523-7060
PURE UUID: adba969f-ddf0-43a6-966c-3d0e2c26085e
ORCID for L.J. Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for R.C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 05 Aug 2008
Last modified: 14 Mar 2019 01:51

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×