Enantiospecific total synthesis of the putative structure of cryptopyranmoscatone B2

Vaithegi, K and Prasad, KR (2018) Enantiospecific total synthesis of the putative structure of cryptopyranmoscatone B2. In: Tetrahedron, 74 (21). pp. 2627-2633.

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Abstract

Total synthesis of THP tethered pyrone containing natural product cryptopyranmoscatone B2 was accomplished from commercially available 2-deoxyribose. The key THP unit was assembled by FeCl3 catalyzed cyclization of an allyl alcohol. Brown allylation and RCM reactions were employed to construct the lactone unit. The synthesis represents the first total synthesis of the putative structure of the natural product.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Ltd
Additional Information:	The copyright for this article belongs to the Elsevier Ltd.
Keywords:	1 2,2 dimethyl 5 (triethylsilyl) oxymethyl 1,3 dioxolan 4 ylpent 4 en 2 ol; 2 deoxyribose; 4 2,2 dimethyl 4 (styryl)tetrahydro 4h 1,3dioxolo4,5 cpyran 6 ylbut 2 en 1 ol; 6 (4 ethoxy 4 oxobut 2 en 1 yl) 2 (styryl)tetrahydro 2h pyran 3,4 diyl bis(4 bromobenzoate); 6 3 2,2 dimethyl 4 (styryl)tetrahydro 4h 1,3dioxolo4,5 cpyran 6 ylprop 1 en 1 yl 5,6 dihydro 2h pyran 2 one; 6 3 4,5 dihydroxy 6 (styryl)tetrahydro 2h pyran 2 ylprop 1 en 1 yl 5,6 dihydro 2h pyran 2 one; 7 2,2 dimethyl 4 (styryl)tetrahydro 4h 1,3dioxolo4,5 cpyran 6 ylhepta 1,5 dien 4 ol; 7 2,2 dimethyl 4 (styryl)tetrahydro 4h 1,3dioxolo4,5 cpyran 6 ylhepta 1,5 dien 4 yl acrylate; allyl alcohol; cryptopyranmoscatone B2; ethyl 4 2,2 dimethyl 4 (styryl)tetrahydro 4h 1,3dioxolo4,5 cpyran 6 ylbut 2 enoate; ethyl 5 hydroxy 6 5 (3 hydroxy 3 phenylprop 1 en 1 yl) 2,2 dimethyl 1,3 dioxolan 4 ylhex 2 enoate; ethyl 5 (tert butyldimethylsilyl)oxy 6 2,2 dimethyl 5 (3 oxo 3 phenylprop 1 en 1 yl) 1,3 dioxolan 4 ylhex 2 enoate; ethyl 5 (tert butyldimethylsilyl)oxy 6 5 (3 hydroxy 3 phenylprop 1 en 1 yl) 2,2 dimethyl 1,3 dioxolan 4 ylhex 2 enoate; ethyl 5 (tert butyldimethylsilyl)oxy 6 5 (hydroxymethyl) 2,2 dimethyl 1,3 dioxolan 4 ylhex 2 enoate; ethyl 5 (tert butyldimethylsilyl)oxy6 2,2 dimethyl 5 (triethylsilyl)oxymethyl 1,3 dioxolan 4 ylhex 2 enoate; ferric chloride; lactone; natural product; tert butyl1 2,2 dimethyl 5 (triethylsilyl)oxymethyl 1,3 dioxolan ylpent 4 en 2 yloxy dimethylsilane; unclassified drug, allylation; Article; catalysis; chemical reaction; chemical structure; cyclization; enantioselectivity; priority journal; ring closing metathesis; synthesis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	11 Aug 2022 10:19
Last Modified:	11 Aug 2022 10:19
URI:	https://eprints.iisc.ac.in/id/eprint/75546

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