Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

Avril E. McCaig, Kevin P. Meldrum, Richard H. Wightman

Research output: Contribution to journalArticle

Abstract

Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.

Original languageEnglish
Pages (from-to)9429-9446
Number of pages18
JournalTetrahedron
Volume54
Issue number32
DOIs
Publication statusPublished - 6 Aug 1998

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Indolizidines
Cycloaddition
Enantiomers
Oxides
Alkenes
nitrones
lentiginosine
pyrroline

Keywords

  • Alkaloids
  • Cycloadditions
  • Indolizidines
  • Pyrrolizidines

Cite this

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title = "Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine",
abstract = "Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.",
keywords = "Alkaloids, Cycloadditions, Indolizidines, Pyrrolizidines",
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year = "1998",
month = "8",
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language = "English",
volume = "54",
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publisher = "Elsevier Limited",
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Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine. / McCaig, Avril E.; Meldrum, Kevin P.; Wightman, Richard H.

In: Tetrahedron, Vol. 54, No. 32, 06.08.1998, p. 9429-9446.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

AU - McCaig, Avril E.

AU - Meldrum, Kevin P.

AU - Wightman, Richard H.

PY - 1998/8/6

Y1 - 1998/8/6

N2 - Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.

AB - Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.

KW - Alkaloids

KW - Cycloadditions

KW - Indolizidines

KW - Pyrrolizidines

U2 - 10.1016/S0040-4020(98)00572-9

DO - 10.1016/S0040-4020(98)00572-9

M3 - Article

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EP - 9446

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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ER -