Synthesis of steroidal derivatives bearing a small ring using a catalytic [2+2] cycloaddition and a ring-contraction rearrangement

被引：7

作者：

Arichi, Norihito ^{[1
]}

Hata, Kenji ^{[1
]}

Takemoto, Yoshiji ^{[1
]}

Yamada, Ken-ichi ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Takasu, Kiyosei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON | 2015年 / 71卷 / 02期

关键词：

Steroids; Cyclopropanes; Cyclobutanes; 2+2] Cycloaddition; Ring contraction; CONFORMATIONALLY RESTRICTED ANALOGS; VITAMIN-D-RECEPTOR; CALCITRIOL; 1-ALPHA; 25-DIHYDROXYVITAMIN D-3; SIDE-CHAIN ANALOGS; SILYL ENOL ETHERS; INHIBITORS; CYCLOBUTANES; VERSATILE; STRATEGY; INDUCE;

D O I：

10.1016/j.tet.2014.11.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fixing conformation by introducing a ring structure is a common strategy in drug development We demonstrate a synthesis that installs a small carbocyclic ring as a structurally-rigid unit in drug lead compounds. Both trans- and cis-cyclobutane rings were constructed in excellent selectivities by controlling the reaction temperature of an EtAlCl2-catalyzed [2+2] cycloaddition between a silyl enol ether and an alpha,beta-unsaturated ester. Spirocyclopropane rings were stereospecifically formed by our previously reported ring-contraction rearrangement of fused cyclobutanols. This strategy allowed stereodivergent access to a new class of steroidal derivatives bearing a small ring. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：233 / 244

页数：12

共 50 条

[1] Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework
Zonker, Benjamin
Becker, Jonathan
Hrdina, Radim
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (18) : 4027 - 4031
[2] Synthesis of spiro-annulated cyclobutane derivatives through ketene [2+2] cycloaddition and ring-rearrangement metathesis
Kotha, Sambasivarao
Pulletikurti, Sunil
[J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2020, 59 (12): : 1875 - 1880
[3] [2+2]-CYCLOADDITION TO OXAZOLE RING
KONDRATEVA, GY
AITZHANOVA, MA
BOGDANOV, VS
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1976, 25 (09): : 2010 - 2010
[4] Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams
Sirindil, Fatih
Miaskiewicz, Solene
Kern, Nicolas
Lalaut, Arno
Felten, Anne-Sophie
Weibel, Jean-Marc
Pale, Patrick
Blanc, Aurelien
[J]. TETRAHEDRON, 2017, 73 (34) : 5096 - 5106
[5] SYNTHESIS OF POLYCYCLIC RING-SYSTEMS VIA INTRAMOLECULAR [2+2]-CYCLOADDITION REACTIONS OF CYCLOPROPENE DERIVATIVES
PADWA, A
RIEKER, W
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 142 - ORGN
[6] SYNTHESIS OF POLYCYCLIC RING-SYSTEMS VIA INTRAMOLECULAR [2+2]-CYCLOADDITION REACTIONS OF CYCLOPROPENE DERIVATIVES
PADWA, A
BLACKLOCK, TJ
RIEKER, WF
[J]. ISRAEL JOURNAL OF CHEMISTRY, 1981, 21 (2-3) : 157 - 163
[7] STUDIES OF REARRANGEMENT REACTION .8. RING-CONTRACTION FROM PYRIDAZINONE DERIVATIVES TO PYRAZOLONE DERIVATIVES .(3)
MAKI, Y
OBATA, K
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1964, 12 (02) : 176 - +
[8] INTRAMOLECULAR [2+2] CYCLOADDITION AND SEQUENTIAL RING EXPANSION
ZHANG, W
COLLINS, MR
MAHMOOD, K
DOWD, P
[J]. TETRAHEDRON LETTERS, 1995, 36 (16) : 2729 - 2732
[9] Triple ring contraction of a [2+2] macrocyclic ligand
Knapton, Matthew
McKee, Vickie
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2013, 69 : 837 - 840
[10] [2+2] CYCLOADDITION REACTIONS OF HOMOAZULENE - A NEW SYNTHESIS OF THE HOMOHEPTALENE RING-SYSTEM
SCOTT, LT
KIRMS, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) : 3530 - 3531

← 1 2 3 4 5 →