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
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
19 June 2008
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), .
(doi:10.1021/ol800767e).
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.
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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: http://eprints.soton.ac.uk/id/eprint/54430
ISSN: 1523-7060
PURE UUID: adba969f-ddf0-43a6-966c-3d0e2c26085e
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Date deposited: 05 Aug 2008
Last modified: 16 Mar 2024 03:00
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Contributors
Author:
I.B. Spurr
Author:
S.C. Kemp
Author:
N.P. Camp
Author:
K.R. Gibson
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