Chiral nonracemic pyranocyclohexanes 7 and 8 and oxepanocyclohexane 11 and 12 were obtained from a single 1,2-isopropylidene-3-O-cyclohexenyl carbohydrate aldehyde 4 via intramolecular nitrile oxide cycloaddition, and were converted to 2-(2'-tetrahydrofuryl)pyran 28, which incorporates the lasalocid skeleton, and the related oxepane derivative 32 respectively, through modification of the furanoside ring by applying 2-O-allyl carbohydrate nitrone cycloaddition.

P ARANI

A BHATTACHARJEE

A BHATTACHARJYA

A PATRA

University of Calcutta (informally known as Calcutta University or CU) is a collegiate public state university located in Kolkata, West Bengal, India.&nbsp;Within India it is recognized as a &quot;Five-Star University&quot; and accredited &quot;A&quot; Grade by National Assessment and Accreditation Council.

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The University of Calcutta has secured the Fifth position among the Universities of India in the prestigious &quot;Indian University Ranking 2019&quot; list, released by the NIRF of the Ministry of Human Resource Development, Government of India.

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It was established on 24 January 1857, and was one of the first institutions in Asia to be established as a multidisciplinary and Western-style university. Its alumni and faculty include several heads of state, heads of government, social reformers, prominent artists, only academy award winner and Dirac medal winner in India, many Fellows of the Royal Society and five Nobel laureates as of 2019 which is highest in South Asia.

University Of Calcutta

Synthesis of chiral pyranocyclohexane, oxepanocyclohexane, and furylpyran and -oxepane systems by the application of intramolecular nitrone and nitrile oxide cycloaddition of carbohydrate derivatives

Tetrahedron

The intramolecular nitrone cycloaddition of three sets of 3-O-allylpyranose and the corresponding homochiral 3-O-allylfuranose-5-aldehyde derivatives was studied; one set derived from D-allose gave rise to only pyran derivatives which were converted to enantiomeric pyranoisoxazolidines via minor degradations. © 1995.

Tetrahedron Letters

Synthesis of enantiomeric pyrans from a 3-O-allylallose derivative by the application of intramolecular nitrone cycloaddition

Chemical Reviews

Asymmetric 1,3-Dipolar Cycloaddition Reactions

Synthesis of optically pure tetrahydrofurans from 2-o-allylglucose derivatives by intramolecular nitrone cycloaddition: preferential formation of a furanoisoxazolidine from penta-o-allylglucose

Synthesis

A New Method for the Generation of Nitrile Oxides and Its Application to the Synthesis of 2-Isoxazolines

Sipholenol and sipholenone, two new triterpenes from the marine sponge (levi).

Journal	Data powered by TypesetTetrahedron
Publisher	Data powered by TypesetPERGAMON-ELSEVIER SCIENCE LTD
ISSN	0040-4020