Stereospecific synthesis of cryptophycin 1

被引：39

作者：

Li, LH ^{[1
]}

Tius, MA ^{[1
]}

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol020001r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A brief stereospecific synthesis of cryptophycin I is described in which (R)-mandelic acid serves as the sole source of asymmetry for unit A. The key step is a hetero-Diels-Alder cycloaddition.

引用

页码：1637 / 1640

页数：4

共 36 条

[11] Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain [J].

Eggen, M ;

Mossman, CJ ;

Buck, SB ;

Nair, SK ;

Bhat, L ;

Ali, SM ;

Reiff, EA ;

Boge, TC ;

Georg, GI .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7792-7799

[12] Rapid entry into the cryptophycin core via an acyl-β-lactam macrolactonization:: Total synthesis of cryptophycin-24 [J].

Eggen, MJ ;

Nair, SK ;

Georg, GI .

ORGANIC LETTERS, 2001, 3 (12) :1813-1815

[13] Stereoselective synthesis of dihydropyran-4-ones via a formal hetero Diels-Alder reaction and ceric ammonium nitrate dehydrogenation [J].

Evans, PA ;

Nelson, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7600-7602

[14] Intramolecular aminolysis of trichloroethyl esters: a mild macrocyclization protocol for the preparation of cryptophycin derivatives [J].

Fray, AH .

TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2777-2781

[15] SYNTHESIS OF (+/-)-PREPINNATERPENE, A BROMODITERPENE FROM THE RED ALGA LAURENCIA-PINNATA YAMADA [J].

FUKUZAWA, A ;

SATO, H ;

MASAMUNE, T .

TETRAHEDRON LETTERS, 1987, 28 (37) :4303-4306

[16] A short enantioselective synthesis of a component of cryptophycin A and arenastatin A [J].

Furuyama, M ;

Shimizu, I .

TETRAHEDRON-ASYMMETRY, 1998, 9 (08) :1351-1357

[17] Enantiospecific total synthesis of the potent antitumor macrolides cryptophycins 1 and 8 [J].

Gardinier, KM ;

Leahy, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7098-7099

[18]

HARAYAMA T, 1978, CHEM PHARM BULL, V26, P1201

[19] HOMOGENEOUS, PALLADIUM(0)-CATALYZED EXCHANGE DEPROTECTION OF ALLYLIC ESTERS, CARBONATES, AND CARBAMATES [J].

JEFFREY, PD ;

MCCOMBIE, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :587-590

[20]

KOBAYASHI M, 1994, CHEM PHARM BULL, V42, P2394

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