Total Synthesis of (+)-Gregatin B and E

被引：24

作者：

Kusakabe, Taichi ^{[1
]}

Kawai, Yasuko ^{[1
]}

Kato, Keisuke ^{[1
]}

机构：

[1] Toho Univ, Fac Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 19期

关键词：

PD(II)-MEDIATED CYCLIZATION-CARBONYLATION; COUPLING REACTIONS; IODIDES; ASPERTETRONIN; DERIVATIVES; GREGATINS; REVISIONS; GRAMININ; ALKYNES; ACCESS;

D O I：

10.1021/ol402472q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+)-gregatin E and a new total synthesis of (+)-gregatin B are described. Key features of our synthetic approach involve a palladium-catalyzed cyclization-methoxycarbonylation of optically active propargylic acetate and a Suzuki-Miyaura coupling or CuTC-mediated coupling reaction. The absolute configuration of (+)-gregatin E (5R,5'S) is proposed.

引用

页码：5102 / 5105

页数：4

共 25 条

[11] Total synthesis of (±)-herbindole (±)-cis-trikentrin B [J].

Jackson, SK ;

Banfield, SC ;

Kerr, MA .

ORGANIC LETTERS, 2005, 7 (07) :1215-1218

[12] A facile access to spiro furanone skeleton based on Pd(II)-mediated cyclization-carbonylation of propargylic esters [J].

Kato, K ;

Nouchi, H ;

Ishikura, K ;

Takaishi, S ;

Motodate, S ;

Tanaka, H ;

Okudaira, K ;

Mochida, T ;

Nishigaki, R ;

Shigenobu, K ;

Akita, H .

TETRAHEDRON, 2006, 62 (11) :2545-2554

[13] Unusual formation of cyclic-orthoesters by Pd(II)-mediated cyclization-carbonylation of propargylic acetates [J].

Kato, K ;

Yamamoto, Y ;

Akita, H .

TETRAHEDRON LETTERS, 2002, 43 (37) :6587-6590

[14] Penicilliols A and B, novel inhibitors specific to mammalian Y-family DNA polymerases [J].

Kimura, Takuma ;

Takeuchi, Toshifumi ;

Kumamoto-Yonezawa, Yuko ;

Ohashi, Eiji ;

Ohmori, Haruo ;

Masutani, Chikahide ;

Hanaoka, Fumio ;

Sugawara, Fumio ;

Yoshida, Hiromi ;

Mizushina, Yoshiyuki .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (05) :1811-1816

[15] A synthesis of α-tocopherol featuring benzyne trapping by an alcohol [J].

Knight, David W. ;

Qing, Xu .

TETRAHEDRON LETTERS, 2009, 50 (26) :3534-3537

[16]

KOBAYASHI K, 1975, TETRAHEDRON LETT, P4119

[17] Ligand effects on the stereochemistry of Stille couplings, as manifested in reactions of Z-alkenyl halides [J].

Lu, Guo-ping ;

Voigtritter, Karl R. ;

Cai, Chun ;

Lipshutz, Bruce H. .

CHEMICAL COMMUNICATIONS, 2012, 48 (69) :8661-8663

[18] Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings [J].

Lu, Guo-Ping ;

Voigtritter, Karl R. ;

Cai, Chun ;

Lipshutz, Bruce H. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) :3700-3703

[19]

Muller S, 1996, SYNLETT, P521

[20] METHANOLYSIS OF DIMETHYL (1-DIAZO-2-OXOPROPYL)PHOSPHONATE - GENERATION OF DIMETHYL (DIAZOMETHYL)PHOSPHONATE AND REACTION WITH CARBONYL-COMPOUNDS [J].

OHIRA, S .

SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :561-564

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