Synthesis of the C(1)−C(12) Segment of Peloruside A by an α-Benzyloxymethyl Ketone Aldol Strategy
作者： Darren W. Engers , Martin J. Bassindale , Brian L. Pagenkopf
DOI: 10.1021/OL036393Z
关键词:
摘要: The C(1)−C(12) segment of 16-membered antitumor macrolide peloruside A has been prepared by a BF3·OEt2-catalyzed Mukaiyama aldol reaction between glucose-derived C(1)−C(7) aldehyde and C(8)−C(12) α-benzyloxymethyl ketone. Exclusive 2,3-anti moderate 3,5-anti/syn facial selectivity (3.5:1) was observed in the reaction. key contains required stereochemistry at carbons two, three, five, efficiently on multigram scales from commercial triacetyl d-glucal.
acs.org
sci-hub.se 参考文章(30)
West Lm, Bäckström Bt, Hood Ka, Northcote Pt, Berridge Mv, Miller Jh, The novel cytotoxic sponge metabolite peloruside A, structurally similar to bryostatin-1, has unique bioactivity independent of protein kinase C. Anti-cancer Drug Design. ,vol. 16, pp. 155- 166 ,(2001)
Peter T. Northcote, St. John Wakefield, Michael V. Berridge, John H. Miller, Lyndon M. West, Berber Rouwé, Kylie A. Hood, Peloruside A, a Novel Antimitotic Agent with Paclitaxel-like Microtubule- stabilizing Activity Cancer Research. ,vol. 62, pp. 3356- 3360 ,(2002)
Michael D. Lewis, Jin Kun Cha, Yoshito Kishi, Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosides Journal of the American Chemical Society. ,vol. 104, pp. 4976- 4978 ,(1982) , 10.1021/JA00382A053
Benjamin List, Richard A. Lerner, Carlos F. Barbas, Proline-Catalyzed Direct Asymmetric Aldol Reactions Journal of the American Chemical Society. ,vol. 122, pp. 2395- 2396 ,(2000) , 10.1021/JA994280Y
Stephen Hanessian, Nike R. Plessas, Reaction of O-benzylidene sugars with N-bromosuccinimide. II. Scope and synthetic utility in the methyl 4,6-0-benzylidenehexopyranoside series Journal of Organic Chemistry. ,vol. 34, pp. 1035- 1044 ,(1969) , 10.1021/JO01256A059
Matthew J. Fisher, Cheryl D. Myers, Jesus Joglar, Shu Hui Chen, Samuel J. Danishefsky, Synthetic studies toward rapamycin : a solution to a problem in chirality merger through use of the Ireland reaction Journal of Organic Chemistry. ,vol. 56, pp. 5826- 5834 ,(1991) , 10.1021/JO00020A026
Bret E. Huff, George S. Sheppard, David A. Evans, Andrew M. Ratz, Mild alcohol methylation procedure for the synthesis of polyoxygenated natural products. Applications to the synthesis of lonomycin A Tetrahedron Letters. ,vol. 35, pp. 7171- 7172 ,(1994) , 10.1016/0040-4039(94)85352-5
Lyndon M. West, Peter T. Northcote, Chris N. Battershill, Peloruside A: A Potent Cytotoxic Macrolide Isolated from the New Zealand Marine SpongeMycalesp. The Journal of Organic Chemistry. ,vol. 65, pp. 445- 449 ,(2000) , 10.1021/JO991296Y
Richard E. Taylor, Meizhong Jin, Toward a total synthesis of peloruside A: enantioselective preparation of the C8-C19 region. Organic Letters. ,vol. 5, pp. 4959- 4961 ,(2003) , 10.1021/OL0358814
William R. Roush, Lance A. Pfeifer, Total Synthesis of Mycalamide A and 7-epi-Mycalamide A Organic Letters. ,vol. 2, pp. 859- 862 ,(2000) , 10.1021/OL005629L