Novel rearrangement of the adduct of 6,6-dimethylfulvene and dichloroketen

One-pot conversion of (±)-7,7-dichloro-4-(1-methylethylidene)-bicyclo[3.2.0]hept-2-en-6-one into dechlorinated γ-lactone

“…We made an attempt to accomplish analogous transformation sequence with structurally similar dichloroketene-dimethylfulvene adduct IV [2]. However, reductive dechlorination of IV with the system Zn-NH 4 Cl-MeOH resulted in the formation of lactone VI instead of expected ketone V (Scheme 2).…”

Syntheses and oxidative transformations of 6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one and its precursors

“…In designing the latter one of the chemofavorable precursors is lactone II which we have prepared from the known bicycle I [5]. In this report we describe the oxidative and some other transformations of lactone II and its precursors aimed at the preparation of more suitable block-synthons for cyclopentanoids, in particular, for developing new routes of the synthesis of the 15-deoxy-Δ 12,14 -prostaglandin J 2 [4] known for its high antitumor and antiviral activity.…”

Reaction of (±)-7,7-dichloro-4-(1-methylethylidene)-bicyclo[3.2.0]hept-2-en-6-one with ozone

“…Although ozone is extremely reactive and nonselective oxidant, available examples of selective ozonolysis convincingly demonstrate wide potential of this procedure [1][2][3][4]. In the present work we made an attempt to build up bicyclic cyclopentenone intermediate product II in one step (Scheme 1) from readily accessible [2 + 2]-adduct I of dimethylfulvene and dichloroketene [5]. For this purpose, we examined the possibility for effecting selective ozonolysis of the exocyclic double bond in compound I. bonds), which precipitated from the solution [6].…”