Total Syntheses of Isomeric Spiroacetal Marine Natural Products Attenols A and B

被引:7
作者
Kumar, Vemula Praveen [1 ]
Kavitha, Nerella [1 ]
Chandrasekhar, Srivari [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
关键词
Natural products; Spiro compounds; Total synthesis; Olefination; ASYMMETRIC HYDRATION; ESTER; ACID; ALCOHOLS; STRATEGY; ANALOGS;
D O I
10.1002/ejoc.201300703
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The convergent total synthesis of two marine natural products, attenols A and B is achieved with excellent stereocontrol. The synthetic route is based on an enantio- and regioselective Sharpless dihydroxylation, palladium(0)-catalyzed reduction to form -hydroxy-1-enoates, stereoselective mCPBA-mediated epoxidation, and Julia-Kocienski olefination.
引用
收藏
页码:6325 / 6334
页数:10
相关论文
共 42 条
[1]   Total synthesis of attenols A and B [J].
Araki, K ;
Suenaga, K ;
Sengoku, T ;
Uemura, D .
TETRAHEDRON, 2002, 58 (10) :1983-1995
[2]   The first total synthesis of (+)-ratjadone [J].
Bhatt, U ;
Christmann, M ;
Quitschalle, M ;
Claus, E ;
Kalesse, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1885-1893
[3]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2011, 28 (02) :196-268
[4]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2010, 27 (02) :165-237
[5]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Hu, Wan-Ping ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2009, 26 (02) :170-244
[6]   A convenient synthesis of chiral β3-amino acids [J].
Chakraborty, TK ;
Ghosh, A .
SYNLETT, 2002, (12) :2039-2040
[7]   Total synthesis of arenamide A and its diastereomer [J].
Chandrasekhar, S. ;
Pavankumarreddy, G. ;
Sathish, K. .
TETRAHEDRON LETTERS, 2009, 50 (49) :6851-6854
[8]   Spirastrellolide B:: The synthesis of southern (C9-C25) region [J].
Chandrasekhar, Srivari ;
Rambabu, Chegondi ;
Reddy, Annareddy Syamprasad .
ORGANIC LETTERS, 2008, 10 (19) :4355-4357
[9]   Total Synthesis of Bengazole A [J].
Chandrasekhar, Srivari ;
Sudhakar, Ambadi .
ORGANIC LETTERS, 2010, 12 (02) :236-238
[10]   Toward Tubulysin: Gram-Scale Synthesis of Tubuvaline-Tubuphenylalanine Fragment [J].
Chandrasekhar, Srivari ;
Mahipal, Bodugam ;
Kavitha, Mitta .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9531-9534