First total synthesis of (±)-methyl gummiferolate using a homoallyl-homoallyl radical rearrangement reaction

被引：22

作者：

Toyota, M ^{[1
]}

Yokota, M ^{[1
]}

Ihara, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 10期

关键词：

D O I：

10.1021/ol990264u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+/-)-methyl gummiferolate (Ib) has been achieved with a high diastereoselectivity. The key steps included the homoallyl-homoallyl radical rearrangement reaction of the enyne 8 to afford the suitably functionalized bicyclo[2.2.2]octane 9 and the intramolecular Diels-Alder reaction of the tetraene 12 for the construction of the AB ring system of Ib.

引用

页码：1627 / 1629

页数：3

共 12 条

[1] REACTIONS OF EPOXIDES .20. PREPARATION AND SOME REACTIONS OF EPOXIDES OF 3- 6- AND 7-METHYLENECHOLESTANE DERIVATIVES
BLACKETT, BN
COXON, JM
HARTSHOR.MP
JACKSON, BLJ
MUIR, CN
[J]. TETRAHEDRON, 1969, 25 (07) : 1479 - &
[2] NATURAL TERPENE DERIVATIVES .250. ADDITIONAL DITERPENES WITH HELIFULVANIC STRUCTURE AND OTHER COMPONENTS OF HELICHRYSUM-CHIONOSPHAERUM
BOHLMANN, F
ABRAHAM, WR
SHELDRICK, WS
[J]. PHYTOCHEMISTRY, 1980, 19 (05) : 869 - 871
[3] A FACILE AND GENERAL-ROUTE TO 4-SUBSTITUTED-2 BUTENOLIDES
CANONNE, P
AKSSIRA, M
LEMAY, G
[J]. TETRAHEDRON LETTERS, 1981, 22 (28) : 2611 - 2614
[4] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS
COREY, EJ
CHAYKOVSKY, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
[5] MICROBIOLOGICAL PREPARATION OF ATISENOLIDES BY GIBBERELLA-FUJIKUROI
FRAGA, BM
GUILLERMO, R
HANSON, JR
[J]. PHYTOCHEMISTRY, 1992, 31 (02) : 503 - 506
[6] FRAGA BM, 1987, PHYTOCHEMISTRY, V26, P2521, DOI 10.1016/S0031-9422(00)83868-6
[7] IMPROVED PREPARATION OF ANGELATE ESTERS
HARTMANN, B
KANAZAWA, AM
DEPRES, JP
GREENE, AE
[J]. TETRAHEDRON LETTERS, 1991, 32 (38) : 5077 - 5080
[8] REGIOSELECTIVE ALKYLATION OF THE POLYFUNCTIONAL NUCLEOPHILE 1-(METHYLTHIO)-3-TRIETHYLSILYLOXYPENTADIENYLLITHIUM
OPPOLZER, W
SNOWDEN, RL
BRINER, PH
[J]. HELVETICA CHIMICA ACTA, 1981, 64 (07) : 2022 - 2028
[9] GUMMIFEROLIC ACID, A NEW ENT-ATIS-16-ENE DITERPENOID FROM MARGOTIA-GUMMIFERA
PINAR, M
RODRIGUEZ, B
ALEMANY, A
[J]. PHYTOCHEMISTRY, 1978, 17 (09) : 1637 - 1640
[10] Total synthesis of (±)-methyl atis-16-en-19-oate via homoallyl-homoallyl radical rearrangement
Toyota, M
Wada, T
Fukumoto, K
Ihara, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (20) : 4916 - 4925

← 1 2 →