STEREOCONTROLLED SYNTHESIS OF KEY INTERMEDIATES IN THE TOTAL SYNTHESIS OF ACETOGENINS OF ANNONACEAE

被引：32
作者：
FIGADERE, B
CHABOCHE, C
PEYRAT, JF
CAVE, A
机构：
[1] Laboratoire de Pharmacognosie, associé au CNRS (BIOCIS) Faculté de Pharmacie
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 50期
关键词：
STEREOSPECIFIC SYNTHESIS; GAMMA-LACTONES; ACETOGENIN; STEREOCHEMICAL RELATIONSHIP ASSIGNMENT;
D O I：
10.1016/S0040-4039(00)61460-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabutanolides 3b and 4b, respectively, have been successfully synthesized from very inexpensive L-glutamic acid The key step of the synthetic sequence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilyloxy)-furan. Stereochemical relationship assignment of the obtained products were deduced from NMR data, and by chemical correlation.
引用
收藏
页码：8093 / 8096
页数：4
相关论文
共 50 条
[21]   Overview of the Synthesis of Optically Active 3-Amino-2-Hydroxy-4-Phenylbutyric Acids, Key Intermediates for Numerous Bioactive Compounds [J].
Jia, Meirong ;
Wei, Tao ;
Yang, Kanghui ;
Xu, WenFang .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2011, 8 (02) :197-210
[22]   A CONCISE SYNTHESIS OF SOLAMIN AND CIS-SOLAMIN, MONO-THF ACETOGENINS FROM ANNONA MURICATA [J].
Makabe, Hidefumi ;
Kuwabara, Asuka ;
Hattori, Yasunao ;
Konno, Hiroyuki .
HETEROCYCLES, 2009, 78 (09) :2369-2376
[23]   A concise enantioselective total synthesis of (+)-epi-muricatacin, using asymmetric hydrogenation/intramolecular iodoetherification as key steps [J].
Kumaraswamy, Gullapalli ;
Ramakrishna, Duggirala ;
Santhakumar, Kondapalli .
TETRAHEDRON-ASYMMETRY, 2010, 21 (05) :544-548
[24]   Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin [J].
Leonelli, Francesca ;
Blesi, Federico ;
Dirito, Paolo ;
Trombetta, Andrea ;
Ceccacci, Francesca ;
La Bella, Angela ;
Migneco, Luisa M. ;
Bettolo, Rinaldo Marini .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) :6871-6876
[25]   A New, Short, and Stereocontrolled Synthesis of C2 -Symmetric 1,2-Diamines [J].
Vemula, Rajender ;
Wilde, Nathan C. ;
Goreti, Rajendar ;
Corey, E. J. .
ORGANIC LETTERS, 2017, 19 (14) :3883-3886
[26]   A NEW METHOD FOR THE STEREOCONTROLLED SYNTHESIS OF DIENAMINE DERIVATIVES USING (NAPHTHALENE)CHROMIUM TRICARBONYL CATALYZED ISOMERIZATION [J].
YAMADA, H ;
SODEOKA, M ;
SHIBASAKI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4569-4574
[27]   Asymmetric Total Synthesis of Inthomycins A, B, and C [J].
Kim, Jae Hyun ;
Song, Yeonghun ;
Kim, Min Jung ;
Kim, Sanghee .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (07) :4795-4806
[28]   Unified Total Synthesis of Madangamines A, C, and E [J].
Suto, Takahiro ;
Yanagita, Yuta ;
Nagashima, Yoshiyuki ;
Takikawa, Shinsaku ;
Kurosu, Yasuhiro ;
Matsuo, Naoya ;
Sato, Takaaki ;
Chida, Noritaka .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (08) :2952-2955
[29]   First stereoselective total synthesis of pectinolide H [J].
Ramesh, D. ;
Shekhar, V. ;
Chantibabu, D. ;
Rajaram, S. ;
Ramulu, U. ;
Venkateswarlu, Y. .
TETRAHEDRON LETTERS, 2012, 53 (10) :1258-1260
[30]   Development of Stereodivergent Synthesis of Skipped Dienes and Application to Unified Total Synthesis of Madangamine Alkaloids [J].
Sato, Takaaki .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2022, 80 (04) :343-356
12345