Stereoselective syntheses of (–)-goniotriol and (–)-8-acetylgoniotriol from D-glycero-D-gulo-heptono-γ-lactone

Tony Kung Ming Shing, Zhao Hui Zhou, Thomas C.W. Mak

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

1-O-Acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 6 has been converted by three consecutive reactions (selective deacetonation, glycol cleavage oxidation, and Wittig reaction) into (Z)-methyl 7-O-acetyl-4,6-O-isopropylidene-7-C-phenyl-D-ido-hept-2-enote 9 which with basic methanol gave 2-deoxy-4,6-O-isopropylidene-3-O-methyl-7-C-phenyl-D-glycero-L-ido-heptono-δ-lactone 10. The structure of 10 has been confirmed by X-ray crystallographic analysis. 1,3-Di-O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 11 has been transformed via a sequence involving selective hydrolysis, deacetylation, glycol cleavage oxidation, and Wittig reaction into (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-gluco-hept-2-enonate 14 which with DBU provided (Z)-5,7-O-isopropylidene-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 16 from which (–)-goniotriol 1 and (–)-8-acetylgoniotriol 2 can be obtained readily. Absolute configurations 8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 3 and 8-O-acetyl-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 4 are assigned to natural goniotriol and 8-acetylgoniotriol respectively.

Original languageEnglish
Pages (from-to)1907-1910
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number15
DOIs
Publication statusPublished - 1992 Jan 1
Externally publishedYes

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Lactones
Glycols
Oxidation
Methanol
goniotriol
propylene
Hydrolysis
X rays

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereoselective syntheses of (–)-goniotriol and (–)-8-acetylgoniotriol from D-glycero-D-gulo-heptono-γ-lactone. / Shing, Tony Kung Ming; Zhou, Zhao Hui; Mak, Thomas C.W.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 15, 01.01.1992, p. 1907-1910.

Research output: Contribution to journalArticle

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title = "Stereoselective syntheses of (–)-goniotriol and (–)-8-acetylgoniotriol from D-glycero-D-gulo-heptono-γ-lactone",
abstract = "1-O-Acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 6 has been converted by three consecutive reactions (selective deacetonation, glycol cleavage oxidation, and Wittig reaction) into (Z)-methyl 7-O-acetyl-4,6-O-isopropylidene-7-C-phenyl-D-ido-hept-2-enote 9 which with basic methanol gave 2-deoxy-4,6-O-isopropylidene-3-O-methyl-7-C-phenyl-D-glycero-L-ido-heptono-δ-lactone 10. The structure of 10 has been confirmed by X-ray crystallographic analysis. 1,3-Di-O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 11 has been transformed via a sequence involving selective hydrolysis, deacetylation, glycol cleavage oxidation, and Wittig reaction into (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-gluco-hept-2-enonate 14 which with DBU provided (Z)-5,7-O-isopropylidene-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 16 from which (–)-goniotriol 1 and (–)-8-acetylgoniotriol 2 can be obtained readily. Absolute configurations 8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 3 and 8-O-acetyl-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 4 are assigned to natural goniotriol and 8-acetylgoniotriol respectively.",
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N2 - 1-O-Acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 6 has been converted by three consecutive reactions (selective deacetonation, glycol cleavage oxidation, and Wittig reaction) into (Z)-methyl 7-O-acetyl-4,6-O-isopropylidene-7-C-phenyl-D-ido-hept-2-enote 9 which with basic methanol gave 2-deoxy-4,6-O-isopropylidene-3-O-methyl-7-C-phenyl-D-glycero-L-ido-heptono-δ-lactone 10. The structure of 10 has been confirmed by X-ray crystallographic analysis. 1,3-Di-O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 11 has been transformed via a sequence involving selective hydrolysis, deacetylation, glycol cleavage oxidation, and Wittig reaction into (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-gluco-hept-2-enonate 14 which with DBU provided (Z)-5,7-O-isopropylidene-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 16 from which (–)-goniotriol 1 and (–)-8-acetylgoniotriol 2 can be obtained readily. Absolute configurations 8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 3 and 8-O-acetyl-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 4 are assigned to natural goniotriol and 8-acetylgoniotriol respectively.

AB - 1-O-Acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 6 has been converted by three consecutive reactions (selective deacetonation, glycol cleavage oxidation, and Wittig reaction) into (Z)-methyl 7-O-acetyl-4,6-O-isopropylidene-7-C-phenyl-D-ido-hept-2-enote 9 which with basic methanol gave 2-deoxy-4,6-O-isopropylidene-3-O-methyl-7-C-phenyl-D-glycero-L-ido-heptono-δ-lactone 10. The structure of 10 has been confirmed by X-ray crystallographic analysis. 1,3-Di-O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 11 has been transformed via a sequence involving selective hydrolysis, deacetylation, glycol cleavage oxidation, and Wittig reaction into (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-gluco-hept-2-enonate 14 which with DBU provided (Z)-5,7-O-isopropylidene-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 16 from which (–)-goniotriol 1 and (–)-8-acetylgoniotriol 2 can be obtained readily. Absolute configurations 8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 3 and 8-O-acetyl-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 4 are assigned to natural goniotriol and 8-acetylgoniotriol respectively.

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