INTRAMOLECULAR AND INTERMOLECULAR HETERO-DIELS-ALDER REACTION .29. HETERO-DIELS-ALDER REACTION OF SUBSTITUTED 1-OXABUTADIENES AND 2-ETHOXYVINYLACETATE - AN ENTRY TO VARIOUS NATURAL OCCURRING CARBOHYDRATES

被引：35

作者：

TIETZE, LF ^{[1
]}

HARTFIEL, U ^{[1
]}

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,TAMMANNSTR 2,W-3400 GOTTINGEN,GERMANY

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)88857-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero-Diels-Alder reaction of 1-oxabutadienes 1a-e bearing an electron-withdrawing group at C-2 or C-3 with (E)- and (Z)-2-ethoxyvinylacetate (2a and 2b) yields the highly functionalized 3,4-dihydro-2H-pyrans 3a-h and 4a-h in mostly excellent yield and modest to good endo/exo selectivity. The cycloadducts 3a and 3c are easily transformed by stereoselective hydrogenation to the ezoaminuroic acid and desosamine derivatives 5 and 7, respectively. The phthalimido-protecting group in 5 and 7 can be removed by reductive cleavage to give 6 and 8. Transformation of 4f by chloro hydrogen exchange affords the corresponding dichloro- as well as the monochloro-compound. © 1990.

引用

页码：1697 / 1700

页数：4

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