Sporolide B: synthetic studies

被引：11
作者：
Gladding, Jeffery A. [1 ]
Bacci, James P. [1 ]
Shaw, Scott A. [1 ]
Smith, Amos B., III [1 ,2 ,3 ]
机构：
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA
[3] Monell Chem Senses Ctr, Philadelphia, PA 19104 USA
来源：
TETRAHEDRON | 2011年 / 67卷 / 35期
基金：
美国国家卫生研究院;
关键词：
Sporolide; Natural products; Synthesis; Benzodiquinane; Hydroquinone; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PROTEASOME INHIBITOR; SALINOSPORAMIDE-A; MICROBIAL METABOLITE; NEUROBLASTOMA-CELLS; SELECTIVE REACTIONS; DIMETHYL-SULFOXIDE; GENERAL-ROUTE; OXIDATION; LACTACYSTIN;
D O I：
10.1016/j.tet.2011.04.094
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Studies directed toward the synthesis of the architecturally complex marine natural product sporolide B are described. Synthetic analysis suggested advanced hydroquinone and benzodiquinane fragments, which upon elaboration were successfully united via an ester linkage. Macrocyclization studies were then carried out, and although a novel macrocyclization product was obtained, subsequent studies revealed that the tertiary hydroxyls at C(6) and C(10) were too sterically encumbered to participate in a successful macrocyclization to furnish sporolide B. (C) 2011 Published by Elsevier Ltd.
引用
收藏
页码：6697 / 6706
页数：10
相关论文
共 56 条
[1]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[2]   Synthetic Studies on the Sporolides: Exploration of the Enediyne Route [J].
Bonazzi, Simone ;
Binaghi, Massimo ;
Fellay, Cindy ;
Wach, Jean-Yves ;
Gademann, Karl .
SYNTHESIS-STUTTGART, 2010, (04) :631-642
[3]   Sporolides A and B:: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica [J].
Buchanan, GO ;
Williams, PG ;
Feling, RH ;
Kauffman, CA ;
Jensen, PR ;
Fenical, W .
ORGANIC LETTERS, 2005, 7 (13) :2731-2734
[4]   OXIDATION OF SUBSTITUTED HYDROQUINONE MONO-ALKYL ETHERS TO PARA-BENZOQUINONE MONOKETALS [J].
BUCHI, G ;
CHU, PS ;
HOPPMANN, A ;
MAK, CP ;
PEARCE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3983-3985
[5]   SELECTIVE REACTIONS BETWEEN PHENOLS AND FORMALDEHYDE - A NOVEL ROUTE TO SALICYLALDEHYDES [J].
CASIRAGHI, G ;
CASNATI, G ;
PUGLIA, G ;
SARTORI, G ;
TERENGHI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1862-1865
[6]   SELECTIVE REACTIONS USING METAL PHENOXIDES .1. REACTIONS WITH FORMALDEHYDE [J].
CASIRAGHI, G ;
CASNATI, G ;
CORNIA, M ;
POCHINI, A ;
PUGLIA, G ;
SARTORI, G ;
UNGARO, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (04) :318-321
[7]   A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with mechanisms distinct from Bortezomib [J].
Chauhan, D ;
Catley, L ;
Li, GL ;
Podar, K ;
Hideshima, T ;
Velankar, M ;
Mitsiades, C ;
Mitsiades, N ;
Yasui, H ;
Letai, A ;
Ovaa, H ;
Berkers, C ;
Nicholson, B ;
Chao, TH ;
Neuteboom, STC ;
Richardson, P ;
Palladino, MA ;
Anderson, KC .
CANCER CELL, 2005, 8 (05) :407-419
[8]   Synthesis of (±)-puraquinonic acid:: An inducer of cell differentiation [J].
Clive, DLJ ;
Sannigrahi, M ;
Hisaindee, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :954-961
[9]  
Corey EJ, 1999, CHEM PHARM BULL, V47, P1
[10]   TOTAL SYNTHESIS OF LACTACYSTIN [J].
COREY, EJ ;
REICHARD, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10677-10678
123456