Total syntheses of (+/-)-cyclophellitol and (1R,6S)-cyclophellitol

被引：31

作者：

Acena, JL ^{[1
]}

Arjona, O ^{[1
]}

Plumet, J ^{[1
]}

机构：

[1] UNIV COMPLUTENSE,FAC QUIM,DEPT QUIM ORGAN 1,E-28040 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo962276o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereodivergent synthesis of (+/-)-cyclophellitol (1) and its unnatural diastereoisomer (1R*,6S*)-cyclophellitol (2), starting from the Diels-Alder adduct of furan and acrylic acid, is reported. The stereochemistry of the key step, the epoxidation of alkene 7, is controlled by the nature of the hydroxyl protecting groups.

引用

页码：3360 / 3364

页数：5

共 46 条

[1] A stereodivergent synthesis of (+/-)-cyclophellitol and (1R*,6S*)-cyclophellitol from the 7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid.
Acena, JL
deAlba, E
Arjona, O
Plumet, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (17) : 3043 - 3044
[2] Polypropionates from 7-oxanorbornene derivatives. A stereoselective and divergent synthesis of fragments with four contiguous chiral centers
Acena, JL
Arjona, O
Leon, M
Plumet, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (49) : 8957 - 8960
[3] STRAIN-DIRECTED BRIDGE CLEAVAGE OF (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - APPLICATION TO THE TOTAL SYNTHESIS OF CARBA-ALPHA-DL-GLUCOPYRANOSE
ACENA, JL
ARJONA, O
DELAPRADILLA, RF
PLUMET, J
VISO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) : 1945 - 1946
[4] A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+/-)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS
ACENA, JL
ARJONA, O
DELAPRADILLA, RF
PLUMET, J
VISO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6419 - 6424
[5] AKIYAMA T, 1991, SYNLETT, P831
[6] PRODUCTION, ISOLATION AND STRUCTURE DETERMINATION OF A NOVEL BETA-GLUCOSIDASE INHIBITOR, CYCLOPHELLITOL, FROM PHELLINUS SP
ATSUMI, S
UMEZAWA, K
IINUMA, H
NAGANAWA, H
NAKAMURA, H
IITAKA, Y
TAKEUCHI, T
[J]. JOURNAL OF ANTIBIOTICS, 1990, 43 (01) : 49 - 53
[7] ATSUMI S, 1993, CANCER RES, V53, P4896
[8] BACKVALL JE, 1987, J AM CHEM SOC, V109, P6396
[9] BACKVALL JE, 1993, J ORG CHEM, V58, P5221
[10] SELENOSULFONATION OF 1,3-DIENES - ONE-POT SYNTHESIS OF 2-(PHENYLSULFONYL)-1,3-DIENES
BACKVALL, JE
NAJERA, C
YUS, M
[J]. TETRAHEDRON LETTERS, 1988, 29 (12) : 1445 - 1448

← 1 2 3 4 5 →

Total syntheses of (+/-)-cyclophellitol and (1R*,6S*)-cyclophellitol

Total syntheses of (+/-)-cyclophellitol and (1R,6S)-cyclophellitol