Convergent formal synthesis of (±)-heliannuols A, K, and L from a common intermediate

被引：21

作者：

Lecornué, F ^{[1
]}

Ollivier, J ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, Lab Carbocycles Assoc CNRS, F-91405 Orsay, France

来源：

SYNLETT | 2004年 / 09期

关键词：

bicyclic compounds; cyclization; enones; heterocycles; organometallic reagents; radical reactions; titanium;

D O I：

10.1055/s-2004-829064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular titanium-mediated cyclopropanation reaction of an oxa-ester bearing a terminal double bond followed by appropriate oxidation and dehydrohalogenation allows easy access to an aryl-fused oxacyclooctenone, an effective precursor of (+/-)-heliannuols A, K and L.

引用

页码：1613 / 1615

页数：3

共 50 条

[1] Strategies for the total asymmetric synthesis of heliannuols K and L:: Scope and limitations
Lecornué, F
Paugam, R
Ollivier, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (12) : 2589 - 2598
[2] Formal syntheses of heliannuols A and D, allelochemicals from Helianthus annus
Tuhina, K
Bhowmik, DR
Venkateswaran, RV
CHEMICAL COMMUNICATIONS, 2002, (06) : 634 - 635
[3] A FORMAL TOTAL SYNTHESIS OF ERYTHROMYCIN-A .2. A CONVERGENT SYNTHESIS OF WOODWARDS CARBAMATE INTERMEDIATE
NAKATA, T
FUKUI, M
OISHI, T
TETRAHEDRON LETTERS, 1988, 29 (18) : 2223 - 2226
[4] Convergent Formal Synthesis of (±)-Roseophilin
Song, Chuanjun
Liu, Hui
Hong, Meiling
Liu, Yuanyuan
Jia, Feifei
Sun, Li
Pan, Zhenliang
Chang, Junbiao
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 704 - 706
[5] Synthesis of spirooxindoles via formal acetylene insertion into a common palladacycle intermediate
Abel-Snape, Xavier
Johnson, Colton E.
Imbriaco, Bianca
Lautens, Mark
CHEMICAL SCIENCE, 2023, 14 (21) : 5650 - 5655
[6] The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate
Boeckman, RK
Clark, TJ
Shook, BC
HELVETICA CHIMICA ACTA, 2002, 85 (12) : 4532 - 4560
[7] Convergent Formal Synthesis of Ecteinascidin 743
Jia, Junhao
Chen, Ruijiao
Jia, Yuanliang
Gu, He
Zhou, Qin
Chen, Xiaochuan
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 13696 - 13706
[8] Formal synthesis of cytostatin by a convergent approach
Salit, Anne-Frederique
Meyer, Christophe
Cossy, Janine
SYNLETT, 2007, (06) : 934 - 938
[9] A convergent formal synthesis of (±)-pumiliotoxin C
Shieh, YS
Yeh, MCP
Rao, UN
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2000, 47 (02) : 283 - 284
[10] Convergent and selective synthesis of pyrrolidinones, piperidinones, dihydropyridinones and pyridinols from a common intermediate - Potential precursors of bioactive products
Jida, Mouhamad
Ollivier, Jean
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (23) : 4041 - 4049

← 1 2 3 4 5 →