Terpestacin core structure. Control of stereochemistry

被引：17

作者：

Berger, GO

Tius, MA

机构：

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

[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 22期

关键词：

D O I：

10.1021/ol052015d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The alpha-hydroxycyclopentenone core structure of terpestacin has been prepared in a model system through an allene ether Nazarov cyclization of an alkylidene-gamma-butyrolactone followed by regio- and stereoselective alkylation reactions. The stereochemistry at C15 (terpestacin numbering) has been used to control stereochemistry at C1 and at C23. The use of E-alkylidene-gamma-butyrolactones extends the scope of the cationic cyclopentannelation reaction.

引用

页码：5011 / 5013

页数：3

共 23 条

[1] Enantioselective synthesis of (-)-terpestacin and structural revision of siccanol using catalytic stereoselective fragment couplings and macrocyclizations
Chan, J
Jamison, TF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) : 10682 - 10691
[2] Synthesis of (-)-terpestacin via catalytic, stereoselective fragment coupling:: Siccanol is terpestacin, not 11-epi-terpestacin
Chan, J
Jamison, TF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) : 11514 - 11515
[3] The Nazarov cyclization in organic synthesis. Recent advances
Frontier, AJ
Collison, C
[J]. TETRAHEDRON, 2005, 61 (32) : 7577 - 7606
[4] Harmata M., 2004, CHEMTRACTS, V17, P416
[5] TERPESTACIN, A NOVEL SYNCYTIUM FORMATION INHIBITOR, ISOLATED FROM ARTHRINIUM SPECIES
IIMURA, S
OKA, M
NARITA, Y
KONISHI, M
KAKISAWA, H
GAO, Q
OKI, T
[J]. TETRAHEDRON LETTERS, 1993, 34 (03) : 493 - 496
[6] Anti-angiogenic activity of terpestacin, a bicyclo sesterterpene from Embellisia chlangdospora
Jung, HJ
Lee, HB
Kim, CJ
Rho, JR
Shin, JH
Kwon, HJ
[J]. JOURNAL OF ANTIBIOTICS, 2003, 56 (05) : 492 - 496
[7] SYNTHESIS AND PHYSIOLOGICAL ACTIVITIES OF BOTH ENANTIOMERS OF CORIOLIC ACID AND THEIR GEOMETRIC ISOMERS
KOBAYASHI, Y
OKAMOTO, S
SHIMAZAKI, T
OCHIAI, Y
SATO, F
[J]. TETRAHEDRON LETTERS, 1987, 28 (34) : 3959 - 3962
[8] Mukaiyama Aldol-Prins cyclization cascade reaction: A formal total synthesis of leucascandrolide A
Kopecky, DJ
Rychnovsky, SD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) : 8420 - 8421
[9] A general strategy for the synthesis of cladiellin diterpenes: Enantioselective total syntheses of 6-acetoxycladiell-7(16),11-dien-3-ol (deacetoxyalcyonin acetate), cladiell-11-ene-3,6,7-triol, sclerophytin A, and the initially purported structure of sclerophytin A
MacMillan, DWC
Overman, LE
Pennington, LD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) : 9033 - 9044
[10] A synthesis of the ring system of terpestacin
Mermet-Mouttet, MP
Gabriel, K
Heissler, D
[J]. TETRAHEDRON LETTERS, 1999, 40 (05) : 843 - 846

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