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C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin

C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin
C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin
A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio- and stereoselective C-H insertion reactions to afford 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-8-ones (18, 26, and 36a/b) with endo,exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis of three endo,exo-furofuran lignans: asarinin (2), fargesin (3), and epimagnolin A (4). En route to the key diazo compounds 24 and 35a/b, a modified procedure for the Ghosez keteniminium-olefin cyclization. was developed, which was required to minimize the decomposition of acid-sensitive functional groups such as electron-rich benzylic ethers that were present in the target compounds 2-4.
metal carbene transformations, stereocontrolled syntheses, furofuran lignans, organic-synthesis, neolignans, esters
0022-3263
6719-6728
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Bataille, Carole J.R.
5803ade3-b90e-4ad2-88e4-daf050ee5472
Bruton, Gordon
aa387dc2-6884-402c-809a-5abf66ec4247
Hinks, Jeremy D.
8d997f2b-107a-43e5-bb60-828e551105b9
Swain, Nigel A.
522cad04-7679-4f30-9b4a-c4351017edad
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Bataille, Carole J.R.
5803ade3-b90e-4ad2-88e4-daf050ee5472
Bruton, Gordon
aa387dc2-6884-402c-809a-5abf66ec4247
Hinks, Jeremy D.
8d997f2b-107a-43e5-bb60-828e551105b9
Swain, Nigel A.
522cad04-7679-4f30-9b4a-c4351017edad

Brown, Richard C.D., Bataille, Carole J.R., Bruton, Gordon, Hinks, Jeremy D. and Swain, Nigel A. (2001) C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin. Journal of Organic Chemistry, 66 (20), 6719-6728. (doi:10.1021/jo015829q).

Record type: Article

Abstract

A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio- and stereoselective C-H insertion reactions to afford 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-8-ones (18, 26, and 36a/b) with endo,exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis of three endo,exo-furofuran lignans: asarinin (2), fargesin (3), and epimagnolin A (4). En route to the key diazo compounds 24 and 35a/b, a modified procedure for the Ghosez keteniminium-olefin cyclization. was developed, which was required to minimize the decomposition of acid-sensitive functional groups such as electron-rich benzylic ethers that were present in the target compounds 2-4.

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More information

Published date: 5 October 2001
Keywords: metal carbene transformations, stereocontrolled syntheses, furofuran lignans, organic-synthesis, neolignans, esters

Identifiers

Local EPrints ID: 19432
URI: https://eprints.soton.ac.uk/id/eprint/19432
ISSN: 0022-3263
PURE UUID: 26e37b1b-9aaf-42d0-b693-cd6749529f50
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 31 Jul 2019 00:49

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