Synthesis of (+)-epiepoformin using the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone

Authors
Shimizu, H Okamura, H Yamashita, N Iwagawa, T Nakatani, M
Citation
H. Shimizu et al., Synthesis of (+)-epiepoformin using the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone, TETRAHEDR L, 42(49), 2001, pp. 8649-8651
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
49
Year of publication
2001
Pages
8649 - 8651
Database
ISI
SICI code
0040-4039(200112)42:49<8649:SO(UTB>2.0.ZU;2-3
Abstract
Asymmetric total synthesis of (+)-epiepoformin was achieved in short steps using the base-catalyzed asymmetric Diels-Alder (DA) reaction of 3-hydroxy- 2-pyrone with chiral acrylate. Since the synthesis produced Ogasawara's int ermediate, it is also presented as a formal synthesis of (-)-theobroxide. ( C) 2001 Elsevier Science Ltd. All rights reserved.