Asymmetric synthesis of the (2S,4S,6S)-2,4,6-trimethylnonyl subunit of siphonarienes
作者： David D. Diaz , Fernando R. P. Crisóstomo , Víctor S. Martín
DOI: 10.1560/Y4CF-YM5A-N6FE-QBWF
关键词: Hydride 、 Chemistry 、 Alcohol 、 Enantioselective synthesis 、 Protein subunit 、 Lewis acids and bases 、 Stereochemistry
摘要: The paper describes an asymmetric approach to the synthesis of (2S,4S,6S)-2,4,6-trimethylnonyl segment siphonarienes. key step used is a newly developed methodology obtain sec-dialkyl acetylenes based on theintramolecular hydride transfer from secondary γ-benzyloxy group with well-defined absolute stereochemistry, ensured by Sharpless epoxidation reaction, cation generated Lewis acid treatment tertiary Co 2 (CO) 6 -complexed propargylic alcohol.
sci-hub.se 参考文章(21)
Denise C. Manker, Mary J. Garson, D. John Faulkner, De Novo biosynthesis of polypropionate metabolites in the marine pulmonate Siphonaria denticulata Journal of The Chemical Society, Chemical Communications. pp. 1061- 1062 ,(1988) , 10.1039/C39880001061
Denzil R. Beukes, Michael T. Davies-Coleman, Novel polypropionates from the South African marine mollusc Siphonaria capensis Tetrahedron. ,vol. 55, pp. 4051- 4056 ,(1999) , 10.1016/S0040-4020(99)00093-9
Manuel Norte, José J. Fernández, Agustín Padilla, Isolation and synthesis of siphonarienal a new polypropionate from Siphonaria grisea Tetrahedron Letters. ,vol. 35, pp. 3413- 3416 ,(1994) , 10.1016/S0040-4039(00)76923-1
M. Carmen Paul, Eva Zubía, Maria J. Ortega, Javier Salvá, New polypropionates from Siphonaria pectinata Tetrahedron. ,vol. 53, pp. 2303- 2308 ,(1997) , 10.1016/S0040-4020(96)01131-3
George M. Whitesides, William F. Fischer, Joseph San Filippo, Robert W. Bashe, Herbert O. House, Reaction of lithium dialkyl- and diarylcuprates with organic halides Journal of the American Chemical Society. ,vol. 91, pp. 4871- 4882 ,(1969) , 10.1021/JA01045A049
Manuel Norte, Fernando Cataldo, Antonio G. González, Matias L. Rodríguez, Catalina . Ruiz-Perez, New metabolites from the marine mollusc siphonaria grisea Tetrahedron. ,vol. 46, pp. 1669- 1678 ,(1990) , 10.1016/S0040-4020(01)81974-8
Uzi Ravid, Robert M. Silverstein, General Synthesis of optically active 4-alkyl (or alkenyl)-γ-lactones from glutamic acid enantiomers Tetrahedron Letters. ,vol. 18, pp. 423- 426 ,(1977) , 10.1016/S0040-4039(01)92655-3
Anthony A Birkbeck, Dieter Enders, The total synthesis of (+)-pectinatone: An iterative alkylation approach based on the SAMP-hydrazone method Tetrahedron Letters. ,vol. 39, pp. 7823- 7826 ,(1998) , 10.1016/S0040-4039(98)01742-0
Michael A. Calter, Wensheng Liao, John A. Struss, Catalytic, asymmetric synthesis of siphonarienal. Journal of Organic Chemistry. ,vol. 66, pp. 7500- 7504 ,(2001) , 10.1021/JO0160367
Manuel Norte, Fernando Cataldo, Antonio G. González, Siphonarienedione and siphonarienolone, two new metabolites from siphonaria grisea having a polypropionate skeleton Tetrahedron Letters. ,vol. 29, pp. 2879- 2880 ,(1988) , 10.1016/0040-4039(88)85236-5