CONFIRMATION BY TOTAL SYNTHESIS OF THE REVISED STRUCTURE OF SPOROL - AN APPLICATION OF CYCLIC THIONOCARBONATE-INITIATED RADICAL CYCLIZATION

被引：9

作者：

ZIEGLER, FE ^{[1
]}

METCALF, CA ^{[1
]}

SCHULTE, G ^{[1
]}

机构：

[1] YALE UNIV,CTR CHEM INSTRUMENTAT,NEW HAVEN,CT 06511

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(00)79828-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The revised structure of sporol is confirmed by the synthesis of the racemate. Tri-n-butylstannyl radical induced fragmentation of a thionocarbonate and subsequent cyclization is employed to prepare a key component in the synthesis.

引用

页码：3117 / 3120

页数：4

共 16 条

[1] Total synthesis of (+/-)-dictamnol by a free radical fragmentation/elimination sequence. Confirmation of its revised structure.
Lange, GL
Merica, A
Chimanikire, M
TETRAHEDRON LETTERS, 1997, 38 (36) : 6371 - 6374
[2] Total synthesis of (n)-dictamnol by a free radical fragmentation/elimination sequence. Confirmation of its revised structure
Lange, G. L.
Merica, A.
Chimanikire, M.
Tetrahedron Letters, 38 (36):
[3] (Alkoxycarbonylamino)methyl radical cyclization and its application to the total synthesis of sibirine
Koreeda, M
Wang, YM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U5 - U5
[4] CYCLIZATION OF POLYENES .40. CONFIRMATION OF THE STRUCTURE OF CERIFEROL AND ITS RELATED SESTERTERPENES BY THE TOTAL SYNTHESIS
FUJIWARA, S
AOKI, M
UYEHARA, T
KATO, T
TETRAHEDRON LETTERS, 1984, 25 (28) : 3003 - 3006
[5] A facile tandem radical cyclization route to propellanes and its application to a total synthesis of modhephene
Lee, HY
Moon, DK
Bahnd, JS
TETRAHEDRON LETTERS, 2005, 46 (09) : 1455 - 1458
[6] Tandem electrocyclic ring opening/radical cyclization: application to the total synthesis of cribrostatin 6
Knueppel, Daniel
Martin, Stephen F.
TETRAHEDRON, 2011, 67 (51) : 9765 - 9770
[7] Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products
Tokuyama, H
Fukuyama, T
CHEMICAL RECORD, 2002, 2 (01): : 37 - 45
[8] INTRAMOLECULAR RADICAL CYCLIZATION OF SILYLACETYLENIC OR OLEFINIC ALPHA-IODO KETONES - APPLICATION TO THE TOTAL SYNTHESIS OF (+/-)-MODHEPHENE
SHA, CK
JEAN, TS
WANG, DC
TETRAHEDRON LETTERS, 1990, 31 (26) : 3745 - 3748
[9] Synthesis of 2,3-disubstituted indoles by radical cyclization with hypophosphorous acid and its application to total synthesis of (±)-catharanthine
Reding, MT
Kaburagi, Y
Tokuyama, H
Fukuyama, T
HETEROCYCLES, 2002, 56 (1-2) : 313 - 330
[10] Stereoselective synthesis of polysubstituted tetrahydrofurans by radical cyclization of epoxides using a transition-metal radical source.: Application to the total synthesis of (±)-methylenolactocin and (±)-protolichesterinic acid
Mandal, PK
Maiti, G
Roy, SC
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09): : 2829 - 2834

← 1 2 →