The synthesis of the (−)-enantiomer of (+)-anhydromyriocin (), the γ-lactone derived from myriocin (thermozymocidin)

Just, George; Payette, Daniel R.

doi:10.1016/s0040-4039(00)78650-3

Cited by 23 publications

(6 citation statements)

References 17 publications

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“…The synthesis of the enantiomer of myriocin was achieved by Wittig reaction of the aldehyde prepared from 86 (Scheme 16) with phosphonium salt 12 (Scheme 1). 9,57 As shown in Scheme 36, oxidation of alcohol 86 with PCC followed by Wittig reaction with phosphonium salt 12 afforded cis-olefin 220. Alkene 220 (>90% cis) was converted into trans isomer 221 in 81% yield by epoxidation of 220 with MCPBA in cyclohexane, chromatographic separation of the major two enantiomers of cis-epoxides, and treatment of the resulting cis-epoxides with lithium diphenylphosphide and iodomethane in tetrahydrofuran.…”

Section: By Wittig or Julia Olefinationmentioning

confidence: 99%

Stereoselective Total Synthesis of Serine Palmitoyl-CoA Transferase Inhibitors

Byun¹,

Lu²,

Bittman³

2006

Synthesis

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S e r i n e P a l m i t o y l -C o A T r a n s f e r a s e I n h i b i t o r s HoeAbstract: This review summarizes the total syntheses of the fungal metabolites mycestericin, myriocin, viridiofungin, sulfamisterin, and sphingofungin. The syntheses are organized into three sections: the preparation of (a) the long chain and (b) the polar head group, and (c) the coupling of the two parts of the molecule. The mechanism of action of these potent inhibitors of serine palmitoyl-CoA transferase, the rate-limiting enzyme in the biosynthesis of sphingolipids, is also briefly described.

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Section: By Wittig or Julia Olefinationmentioning

confidence: 99%

Stereoselective Total Synthesis of Serine Palmitoyl-CoA Transferase Inhibitors

Byun¹,

Lu²,

Bittman³

2006

Synthesis

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“…The synthesis of the enantiomer 857 of this compound from L-arabinose has been described (360). The synthesis of the enantiomer 857 of this compound from L-arabinose has been described (360).…”

Section: Chiral Carbon Fragments and Their Use In Synthesis 133mentioning

confidence: 99%

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

Scott

1984

Asymmetric Synthesis

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“…Upon N-acylation the amino acids (6) and (1 3) cyclized to the corresponding 1,4-Iactones (5) and (I 2).…”

Section: -Benzoylamino-2-deoxy-2-hydroxymethyl-d-hexono-14-lactonesmentioning

confidence: 99%

“…The residue was taken up in CH2C12, and the solution washed with 5% aqueous NaHC0, (5 x 10 ml) and then evaporated. (5).-This compound was synthesized starting from the amino acid (6) (809 mg, 3.595 mmol) with the perbenzoylation-methanolysis method above described. 2-Benzoylamino-2-benzo yl oxymethyl-2-deoxy-3,5,6-tri-0-benzoyl-Dmannono-1,4-lactone (2.1 5 g, 82%) was characterized as follows: m.p.…”

Section: -Benzoylamino-2-deoxy-2-hydroxymethyl-~-glucono-14lactone (1...mentioning

confidence: 99%