CYCLIZATION OF POLYENES .49. CYCLIZATION OF EPOXYNEOCEMBRENE DERIVATIVES TO SECOTRINERVITANES

被引：11

作者：

HIRUKAWA, T ^{[1
]}

KOARAI, A ^{[1
]}

KATO, T ^{[1
]}

机构：

[1] SCI UNIV TOKYO,FAC SCI,DEPT CHEM,1-3 KAGURAZAKA,SHINJYUKU KU,TOKYO 162,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four stereoisomers of epoxyneocembrene derivatives 5-8 were treated with BF3.OEt2 as potential model reactions for the proposed biogenesis of secotrinervitane-type diterpenoids (Scheme I). Two of them (5 and 6) afforded secotrinervitane derivatives, while the remaining isomers 7 and 8 gave no cyclization products (Table I). The natural product, secotrinervitene-2-beta,3-alpha-diol (2a) was synthesized from 5 in dl-form.

引用

页码：4520 / 4525

页数：6

共 50 条

[41] PYRIDYLMETHYLINDANOL DERIVATIVES - REDUCTIVE CYCLIZATION TO OCTAHYDROINDENOINDOLIZINE
SAM, J
PLAMPIN, JN
ALWANI, DW
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (12): : 4543 - &
[42] CYCLOPOLYMERIZATION - CYCLIZATION OF DIALLYLCYANAMIDE TO PYRROLIDINE DERIVATIVES
BRACE, NO
JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1970, 8 (08): : 2091 - &
[43] STERIC REQUIREMENTS IN THE CYCLIZATION OF NAPHTHALENE DERIVATIVES
DJERASSI, C
PETTIT, GR
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (04): : 393 - 396
[44] SYNTHESIS AND INTRAMOLECULAR CYCLIZATION OF BISTHIADIAZINYLMETHANE DERIVATIVES
GOYA, P
MARTINEZ, A
OCHOA, C
STUD, M
JIMENO, ML
FOCESFOCES, C
CANO, FH
MARTINEZRIPOLL, M
TETRAHEDRON, 1985, 41 (15) : 3105 - 3116
[45] CYCLIZATION REACTIONS CONDUCTED ON DERIVATIVES OF AZIRIDINOTETRAHYDROFURANS
CLEOPHAX, J
HILDESHE.J
SEPULCHR.AM
GERO, SD
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1968, 266 (10): : 720 - &
[46] CYCLIZATION OF CHALCONES TO ISOXAZOLE AND PYRAZOLE DERIVATIVES
Voskiene, A.
Mickevicius, V.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (12) : 1485 - 1488
[47] CYCLIZATION OF STABLE AZIDOAZOMETHINES TO TETRAZOLE DERIVATIVES
PLENKIEWICZ, J
HETEROCYCLES, 1978, 9 (10) : 1518 - 1518
[48] THE CYCLIZATION OF DISUBSTITUTED PENTENOIC ACID DERIVATIVES
RAFFAUF, RF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (17) : 4460 - 4461
[49] BIOMIMETIC CYCLIZATION OF HEDYCARYOL DERIVATIVES - UNEXPECTED CYCLIZATION OF PHENYL SULFIDES WITH METHYL-IODIDE
KODAMA, M
SHIMADA, K
ITO, S
TETRAHEDRON LETTERS, 1981, 22 (16) : 1523 - 1526
[50] Cyclization/Oxygenation Scheme for the Conversion of Polyenes into C3-Oxygenated Polycycles
Geier, Michael J.
Gagne, Michel R.
ORGANOMETALLICS, 2013, 32 (02) : 380 - 383

← 1 2 3 4 5 →