| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345330 | Tetrahedron: Asymmetry | 2015 | 6 Pages |
A chiron approach to the synthesis of the proposed structure of pestalotioprolide A, a 14-membered unsaturated macrolide isolated from the mangrove-derived fungus Pestalotiopsis sp. PSU-MA119, starting from d-(+)-gluconic acid δ-lactone is described. The key strategies to assemble the macrolactone include Yamaguchi esterification and ring-closing metathesis.
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(S)-1-((4R,4′R,5R)-2,2,2′,2′-Tetramethyl-4,4′-bi(1,3-dioxolan)-5-yl)prop-2-en-1-olC13H22O5[α]D25 = −25.4 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,R,R,R)
tert-Butyldiphenyl((S)-1-((4R,4′R,5S)-2,2,2′,2′-tetramethyl-4,4′-bi(1,3-dioxolan)-5-yl)allyloxy)silaneC29H40O5Si[α]D25 = −3.3 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,R,R)
(R)-1-((4R,5S)-5-((S)-1-(tert-Butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diolC26H36O5Si[α]D25 = −16.3 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,R,R)
(R)-2-((4R,5S)-5-((S)-1-(tert-Butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl benzoateC33H40O6Si[α]D25 = −8.8 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,R,R)
(R)-2-(tert-Butyldimethylsilyloxy)-2-((4S,5S)-5-((S)-1-(tert-butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl benzoateC39H54O6Si2[α]D25 = −3.5 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,S,R)
(R)-2-(tert-Butyldimethylsilyloxy)-2-((4S,5S)-5-((S)-1-(tert-butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanolC32H50O5Si2[α]D25 = +5.8 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,S,R)
(S)-2-(tert-Butyldimethylsilyloxy)-2-((4S,5S)-5-((S)-1-(tert-butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehydeC32H48O5Si2[α]D25 = −3.7 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,S,S)
(R,E)-Ethyl 4-(tert-butyldimethylsilyloxy)-4-((4S,5S)-5-((S)-1-(tert-butyldiphenyl-silyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoateC36H54O6Si2[α]D25 = −2.7 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,S,R,E)
(R,E)-4-(tert-Butyldimethylsilyloxy)-4-((4S,5S)-5-((S)-1-(tert-butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoic acidC34H50O6Si2[α]D25 = −1.7 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactoneAbsolute configuration: (S,S,S,R,E)
(R,E)-((S)-Hept-6-en-2-yl)4-(tert-butyldimethylsilyloxy)-4-((4S,5S)-5-((S)-1-(tert-butyl-diphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoateC41H62O6Si2[α]D25 = +2.4 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactone and l-(−)-malic acidAbsolute configuration: (S,S,S,R,E,S)
(R,E)-((S)-Hept-6-en-2-yl)4-hydroxy-4-((4R,5R)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoateC19H30O6[α]D25 = −71.8 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactone and l-(−)-malic acidAbsolute configuration: (S,R,R,R,E,S)
(3aR,4R,5E,9S,13Z,15S,15aR)-4,15-Dihydroxy-2,2,9-trimethyl-9,10,11,12,15,15a-hexahydro-3aH-[1,3]dioxolo[4,5-f][1]oxacyclotetradecin-7(4H)-oneC17H26O6[α]D25 = −69.6 (c 0.1, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactone and l-(−)-malic acidAbsolute configuration: (S,R,R,R,E,S,Z)
(3E,5R,6R,7R,8S,9Z,14S)-5,6,7,8-Tetrahydroxy-14-methyloxacyclotetradeca-3,9-dien-2-oneC14H22O6[α]D25 = −127.6 (c 0.15, CHCl3)Source of chirality: d-(+)-gluconic acid δ-lactone and l-(−)-malic acidAbsolute configuration: (S,R,R,R,E,S,Z)
