Asymmetric Total Synthesis of Lobophopyranone A and B

被引:0
作者
Reddy, G. Sudhakar [1 ,2 ]
Choudhury, Utkal Mani [1 ,2 ]
Keerthana, H. Sai [1 ]
Naik, K. Charan [1 ,2 ]
Mohapatra, Debendra K. [1 ,2 ]
机构
[1] CSIR Indian Inst Chem Technol, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源
SYNTHESIS-STUTTGART | 2025年 / 57卷 / 01期
关键词
lobophopyranone; natural products; asymmetric synthesis; Keck-Maruoka allylations; Sakurai allylation; acid-mediated cyclization; IODOXYBENZOIC ACID IBX; BIS(((S)-BINAPHTHOXY)(ISOPROPOXY)TITANIUM) OXIDE; LOBOPHORA-VARIEGATA; SECONDARY ALCOHOLS; ORGANIC-SYNTHESIS; CYCLIC PEROXIDES; ALLYLATION; OXIDATION; METABOLITES; CLEAVAGE;
D O I
10.1055/a-2338-4462
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first asymmetric total synthesis and structural confirmation of lobophopyranone A and B have been accomplished from commercially available starting materials. Reagent-controlled Keck-Maruoka allylation, Grignard reaction, chelation-controlled Sakurai allylation, and acid-mediated one-step TBS ether deprotection followed by cyclization are the crucial stages in this synthesis that create the 2,6-disubstituted dihydropyranone component.
引用
收藏
页码:99 / 108
页数:10
相关论文
共 47 条
[1]   Tenuipyrone, a Novel Skeletal Polyketide from the Entomopathogenic Fungus, Isaria tenuipes, Cultivated in the Presence of Epigenetic Modifiers [J].
Asai, Teigo ;
Chung, Yu-Ming ;
Sakurai, Hiroaki ;
Ozeki, Tomoji ;
Chang, Fang-Rong ;
Yamashita, Kouwa ;
Oshima, Yoshiteru .
ORGANIC LETTERS, 2012, 14 (02) :513-515
[2]   Structure Elucidation and Absolute Stereochemistry of Isomeric Monoterpene Chromane Esters [J].
Batista, Joao M., Jr. ;
Batista, Andrea N. L. ;
Mota, Jonas S. ;
Cass, Quezia B. ;
Kato, Massuo J. ;
Bolzani, Vanderlan S. ;
Freedman, Teresa B. ;
Lopez, Silvia N. ;
Furlan, Maysa ;
Nafie, Laurence A. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2603-2612
[3]   Two Molecules of Lobophorolide Cooperate to Stabilize an Actin Dimer Using Both Their "Ring" and "Tail" Region [J].
Blain, J. Craig ;
Mok, Yee-Foong ;
Kubanek, Julia ;
Allingham, John S. .
CHEMISTRY & BIOLOGY, 2010, 17 (08) :802-807
[4]   The Tropical Brown Alga Lobophora variegata: A Source of Antiprotozoal Compounds [J].
Cantillo-Ciau, Zulema ;
Moo-Puc, Rosa ;
Quijano, Leovigildo ;
Freile-Pelegrin, Yolanda .
MARINE DRUGS, 2010, 8 (04) :1292-1304
[5]   Antileishmanial cyclic peroxides from the Palauan sponge Plakortis aff. angulospiculatus [J].
Compagnone, RS ;
Piña, IC ;
Rangel, HR ;
Dagger, F ;
Suárez, AI ;
Reddy, MVR ;
Faulkner, DJ .
TETRAHEDRON, 1998, 54 (13) :3057-3068
[6]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[7]   Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence [J].
Danishefsky, SJ ;
Bilodeau, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1380-1419
[8]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[9]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[10]   Oxazoline N-oxide-mediated [2+3] cycloadditions.: Application to a synthesis of (-)-tetrahydrolipstatin [J].
Dirat, O ;
Kouklovsky, C ;
Langlois, Y .
ORGANIC LETTERS, 1999, 1 (05) :753-755