Un ruta de acceso estereodivergente a carbaazúcares naturales a partir de derivados (Fenilsulfonil)-7 -oxabiciclo[2.2.1 ]heptane. Síntesis total de ( ± )-V alidarnina y de sus C I y C2 estereoisómeros
Abstract
La epoxidación nucleofilica estereocontrolada de ciclohexenil sulfonas polidroxiladas,
obtenidas a partir de (fenilsulfonil)-7-oxabiciclo[2,2, l ] heptano s conduce a la síntesis total
del antibiótico validarnina y sus tres diastereoisómeros. La diastereoselectividad de la
epoxidación puede controlarse facilrnente mediante la elección del grupo protector del
hidroxilo. La apertura del anillo de las epoxisulfonas resultantes, seguida de la introducción
estereocontrolada de un precursor del grupo amino, conduce a los cuatro diastereosiómeros
en C-l y C-2 de l-aminocarbaazúcares.
Downloads
References
47:4571-4578. b) LEY, S. V. and YEUNG, L. L. (1992): Synlett, pp. 291-292. e)
REDLICH, H.; SUDAU, W.; SZARDENINGS, A. K. and VOLLERTHUN, R. (1992):
Carbohydr. Res., 226:57-58. d) CAl, S.; STROUD, M. R; HAKOMORl, S. and TOYOKUNI,
T. (1992): J. Org. Chem., 57:6693-6696. e) PINGLI, L. and VANDEWALLE, M. (1994):
Synlett, pp. 228-230.
HORn, S.; IWASA, T.; MIZUTA, E. and KAMEDA, Y. (1971): J. Antibiot., 24:59-63 .
KAMEDA, Y.; ASANO, N.; YOSHlKAWA, M.; TAKEUCHl, M.; YAMAGUCHl, T.;
MATSUl, K.; HORlI, S. and FUKASE, H. (1984): J. Antibiot., 37:1301-1307.
IWASA, T.; YAMAMOTO, H. and SHlBATA, M. (1970): J. Antibiot., 23:595-602.
ASANO, N.; YAMAGUCHl, T.; KAMEDA, Y. and MATSUl, K. (1987): J. Antibiot.,
40:526-532.
a) SUAMI, T.; OGA WA, S.; NAKAMOTO, K. and KASAHARA, 1. (1977): Carbohydr.
Res., 58:240-244. b) PAULSEN, H. and HEIKER, F. R. ( 1980): Angew. Chem. Int. Ed.
Engl., 19:904-905. e) SCHMIDT, R R. and KGHN, A. (1987): Angew. Chem. Int. Ed.
Engl., 26:482-483. d) OGAWA, S.; SUZUKI, M. and TONEGAWA, T. (1988): Bull.
Chem. Soco Jpn., 61:1824-1826. e) YOSHlKAWA, M.; CRA, B. c.; OKAlCHl, Y.;
TAKINAMI, Y.; YOKOKAWA, Y. and KITAGAWA, 1. (1988): Chem. Pharm. Bull.,
36:4236-4239. t) TAKAHASHI, T.; KOTSUBO, H.; IYOBE, A.; NAMIKI, T. and
KOIZUMI, T. (1990): Chem. Soco Perkin Trans., 1:3065-3072. g) KNAPP, S.; NAUGHTON,
A. B. J. and MURALI DHAR, T. G. (1992): Tetrahedron Lett. , 33: 1025-1028. h) FUKASE,
H. and HORn, S. (1992): J. Org. Chem., 57:3651-3658.
ACEÑA, J. L.; ARJONA, O.; FERNÁNDEZ DE LA PRADILLA, R.; PLUMET, J. and
VISO, A. (1992): J. Org. Chem., 57: 1945-1946.
For se1ected reviews of the chemistry of 7-oxanorbomenic systems, see: a) VOGEL, P.
(1990) : Bull. Soco Chim. Belg., 99:395-439. b) VOGEL, P.; FATTORl, D.; GASPARINI,
F. and LE DRlAN, C. (1990): Synlett, pp. 173-1 85. For recents applications of these
Downloads
Published
How to Cite
Issue
Section
License
The articles, which are published in this journal, are subject to the following terms in relation to the rights of patrimonial or exploitation:
- The authors will keep their copyright and guarantee to the journal the right of first publication of their work, which will be distributed with a Creative Commons BY-NC-SA 4.0 license that allows third parties to reuse the work whenever its author, quote the original source and do not make commercial use of it.
b. The authors may adopt other non-exclusive licensing agreements for the distribution of the published version of the work (e.g., deposit it in an institutional telematic file or publish it in a monographic volume) provided that the original source of its publication is indicated.
c. Authors are allowed and advised to disseminate their work through the Internet (e.g. in institutional repositories or on their website) before and during the submission process, which can produce interesting exchanges and increase citations of the published work. (See The effect of open access).
