Abstract
An efficient synthesis of cyclopropyl-lactone containing fragment of solandelactones has been achieved via ring-closing olefinic metathesis reaction. Grubbs’ second generation RuCl2(=CHPh)(PCy3)(IEMS) catalyst has been successfully and efficiently utilized in the construction of eight-membered lactone ring with cis-double bond present in solandelactones.
Highlights
The formation of rings represents a central theme in natural product synthesis
We previously developed a highly convergent approach for the formal synthesis of solandelactones,3a which is crucial to the work described
Our previous synthesis provided a method for the preparation of compound 7.3a As outlined in the retrosynthetic analysis (Scheme 1), the chiral pool D-glyceraldehyde [8] was obtained from D-mannitol following the literature precedent
Summary
The formation of rings represents a central theme in natural product synthesis. A number of natural products contain medium-sized saturated as well as unsaturated lactone rings. This class of compounds continues to generate intense interest from synthetic organic chemists due to their interesting structural features associated with important biological activities. A number of natural products contain medium-sized saturated as well as unsaturated lactone rings.2 This class of compounds continues to generate intense interest from synthetic organic chemists due to their interesting structural features associated with important biological activities. Solandelactones [1] belonging to the growing class of oxylipins containing a transbifunctional cyclopropane ring and fatty acid lactones of marine origin were isolated from the hydroid Solanderia secunda of Korean waters and their structures were elucidated by exhaustive spectroscopic and chemical method.. Solandelactones [1] belonging to the growing class of oxylipins containing a transbifunctional cyclopropane ring and fatty acid lactones of marine origin were isolated from the hydroid Solanderia secunda of Korean waters and their structures were elucidated by exhaustive spectroscopic and chemical method.9 Their structural uniqueness as well as intriguing biological activities led us to synthesize them in a suitable manner.
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