Stereoselective total synthesis of the natural (+)-lasonolide A

被引：20

作者：

Kang, SH ^{[1
]}

Kang, SY

Choi, HW

Kim, CM

Jun, HS

Youn, JH

机构：

[1] Korea Adv Inst Sci & Technol, Sch Mol Sci, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea

[2] Sun Moon Univ, Dept Chem Engn, Chungnam 336840, South Korea

来源：

SYNTHESIS-STUTTGART | 2004年 / 07期

关键词：

asymmetric synthesis; diastereomeric differentiation; macrocyclization; natural products; total synthesis;

D O I：

10.1055/s-2004-822340

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C-22 quaternary chiral center, use of a disulfone equivalent for elongation of the C-15-C-17 three-carbon chain as well as introduction of the two trans olefins at C-15 and C-17, iodocyclization for the upper THP, Michael addition for the bottom THP, and intramolecular Horner-Emmons olefination for the 20-membered macrolactone.

引用

收藏

页码：1102 / 1114

页数：13

相关论文

共 32 条

[21] STEREODIVERGENCE IN AN INTRAMOLECULAR HORNER-EMMONS MACROCYCLIZATION - EFFECT OF REACTION CONDITIONS ON PRODUCT DISTRIBUTION [J].

MORINFOX, ML ;

LIPTON, MA .

TETRAHEDRON LETTERS, 1993, 34 (49) :7899-7902

[22] CARBOHYDRATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 16-MEMBERED-RING MACROLIDE ANTIBIOTICS .6. TOTAL SYNTHESIS OF O-MYCINOSYLTYLONOLIDE - COUPLING OF KEY INTERMEDIATES AND MACROCYCLIZATION [J].

NICOLAOU, KC ;

SEITZ, SP ;

PAVIA, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) :2030-2031

[23] Total synthesis of swinholide A, preswinholide A, and hemiswinholide A [J].

Nicolaou, KC ;

Patron, AP ;

Ajito, K ;

Richter, PK ;

Khatuya, H ;

Bertinato, P ;

Miller, RA ;

Tomaszewski, MJ .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (07) :847-868

[24] Asymmetric synthesis of the C(18)-C(24) unit of lasonolide A [J].

Nowakowski, M ;

Hoffmann, HMR .

TETRAHEDRON LETTERS, 1997, 38 (06) :1001-1004

[25] OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS [J].

PAPPO, R ;

ALLEN, DS ;

LEMIEUX, RU ;

JOHNSON, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :478-479

[26] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDEHYDE ADDITION-REACTIONS OF 2-ALLYL-1,3,2-DIOXABOROLANE-4,5-DICARBOXYLIC ESTERS, A USEFUL CLASS OF TARTRATE ESTER MODIFIED ALLYLBORONATES [J].

ROUSH, WR ;

WALTS, AE ;

HOONG, LK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) :8186-8190

[27] DIRECT SYNTHESIS OF Z-UNSATURATED ESTERS - A USEFUL MODIFICATION OF THE HORNER-EMMONS OLEFINATION [J].

STILL, WC ;

GENNARI, C .

TETRAHEDRON LETTERS, 1983, 24 (41) :4405-4408

[28] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .9. TOTAL SYNTHESIS OF TYLONOLIDE, THE AGLYCONE OF THE 16-MEMBERED RING MACROLIDE TYLOSIN, FROM D-GLUCOSE - SELECTIVE APPLICATION OF MPM AND DMPM PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].

TANAKA, T ;

OIKAWA, Y ;

HAMADA, T ;

YONEMITSU, O .

TETRAHEDRON LETTERS, 1986, 27 (31) :3651-3654

[29]

Tidwell T.T., 1990, ORG REACT, V39, P297, DOI [DOI 10.1002/0471264180.OR039.03, 10.1002/0471264180.or039.03]

[30] Total synthesis of rutamycin B, a macrolide antibiotic from Streptomyces aureofaciens [J].

White, JD ;

Hanselmann, R ;

Jackson, RW ;

Porter, WJ ;

Ohba, Y ;

Tiller, T ;

Wang, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :5217-5231

← 1 2 3 4 →