Concise total synthesis of botryolide B

作者: Debendra K. Mohapatra , Gonela Umamaheshwar , M. Mallikarjuna Rao , Deivasigamani Umadevi , Jhillu S. Yadav

DOI: 10.1039/C3RA44478C

关键词: Botryolide BRing (chemistry)Fragment (computer graphics)Total synthesisRing-closing metathesisAlcoholYield (chemistry)Carboxylic acidStereochemistryChemistry

摘要: An efficient total synthesis of botryolide B was achieved in 9 longest linear steps with 22% overall yield via esterification a carboxylic acid an alcohol fragment and ring closing metathesis (RCM) reaction as pivotal to construct the macrolactone system. Our novel approach for 2-alkene-1,5-diol by followed reductive opening strategy, whereas accessed from commercially available (R)-(+)-α-hydroxy-γ-butyrolactone three steps.

参考文章(32)
Scott E. Schaus, Bridget D. Brandes, Jay F. Larrow, Makoto Tokunaga, Karl B. Hansen, Alexandra E. Gould, Michael E. Furrow, Eric N. Jacobsen, Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIII Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols Journal of the American Chemical Society. ,vol. 124, pp. 1307- 1315 ,(2002) , 10.1021/JA016737L
Zhengqing Ye, Tingyi Gao, Gang Zhao, Enantioselective total synthesis of the proposed structure of macrolide iriomoteolide-1b Tetrahedron. ,vol. 67, pp. 5979- 5989 ,(2011) , 10.1016/J.TET.2011.06.025
Joëlle Prunet, Recent Methods for the Synthesis of (E)-Alkene Units in Macrocyclic Natural Products Angewandte Chemie International Edition. ,vol. 42, pp. 2826- 2830 ,(2003) , 10.1002/ANIE.200301628
Antonella De Mico, Roberto Margarita, Luca Parlanti, Andrea Vescovi, Giovanni Piancatelli, A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds Journal of Organic Chemistry. ,vol. 62, pp. 6974- 6977 ,(1997) , 10.1021/JO971046M
Robert H. Grubbs, Sukbok Chang, Recent advances in olefin metathesis and its application in organic synthesis Tetrahedron. ,vol. 54, pp. 4413- 4450 ,(1998) , 10.1016/S0040-4020(97)10427-6
J.S. Yadav, N. Niranjan Kumar, M. Sridhar Reddy, A.R. Prasad, Stereoselective synthesis of tarchonanthuslactone via the Prins cyclisation Tetrahedron. ,vol. 63, pp. 2689- 2694 ,(2007) , 10.1016/J.TET.2007.01.019
Debendra K. Mohapatra, Dhondi K. Ramesh, Michael A. Giardello, Mukund S. Chorghade, Mukund K. Gurjar, Robert H. Grubbs, Protecting group directed ring-closing metathesis (RCM): the first total synthesis of an anti-malarial nonenolide Tetrahedron Letters. ,vol. 48, pp. 2621- 2625 ,(2007) , 10.1016/J.TETLET.2007.02.040
B. Chennakesava Reddy, H.M. Meshram, A concise stereoselective total synthesis of Botryolide B Tetrahedron Letters. ,vol. 51, pp. 4020- 4022 ,(2010) , 10.1016/J.TETLET.2010.05.079
Arlene A. Sy, Dale C. Swenson, James B. Gloer, Donald T. Wicklow, Botryolides A-E, decarestrictine analogues from a fungicolous Botryotrichum sp. (NRRL 38180). Journal of Natural Products. ,vol. 71, pp. 415- 419 ,(2008) , 10.1021/NP070610D