Multi-step rearrangement mechanism for acetyl cedrene to the hydrocarbon follower

Shashikumar Keshav Paknikar, Fadhil S. Kamounah, Poul Erik Hansen, Murzban Sorab Wadia

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Conversion of acetyl cedrene (2) to its follower (3) using acetic anhydride and polyphosphoric acid involves a multi-step cationic molecular rearrangement, which is consistent with deuteriation and 1-13C labeling studies of acetyl cedrene. The key step involves cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement.
Original languageEnglish
JournalChemistry of Natural Compounds
Volume53
Issue number4
Pages (from-to)661-664
Number of pages4
ISSN0009-3130
DOIs
Publication statusPublished - 2017

Keywords

  • biosynthetic pathway
  • α -cedrene
  • deuterium exchange
  • acetylation
  • cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement (CCR)

Cite this

Paknikar, Shashikumar Keshav ; Kamounah, Fadhil S. ; Hansen, Poul Erik ; Wadia, Murzban Sorab . / Multi-step rearrangement mechanism for acetyl cedrene to the hydrocarbon follower. In: Chemistry of Natural Compounds. 2017 ; Vol. 53, No. 4. pp. 661-664.
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abstract = "Conversion of acetyl cedrene (2) to its follower (3) using acetic anhydride and polyphosphoric acid involves a multi-step cationic molecular rearrangement, which is consistent with deuteriation and 1-13C labeling studies of acetyl cedrene. The key step involves cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement.",
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Multi-step rearrangement mechanism for acetyl cedrene to the hydrocarbon follower. / Paknikar, Shashikumar Keshav ; Kamounah, Fadhil S.; Hansen, Poul Erik; Wadia, Murzban Sorab .

In: Chemistry of Natural Compounds, Vol. 53, No. 4, 2017, p. 661-664.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Multi-step rearrangement mechanism for acetyl cedrene to the hydrocarbon follower

AU - Paknikar, Shashikumar Keshav

AU - Kamounah, Fadhil S.

AU - Hansen, Poul Erik

AU - Wadia, Murzban Sorab

PY - 2017

Y1 - 2017

N2 - Conversion of acetyl cedrene (2) to its follower (3) using acetic anhydride and polyphosphoric acid involves a multi-step cationic molecular rearrangement, which is consistent with deuteriation and 1-13C labeling studies of acetyl cedrene. The key step involves cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement.

AB - Conversion of acetyl cedrene (2) to its follower (3) using acetic anhydride and polyphosphoric acid involves a multi-step cationic molecular rearrangement, which is consistent with deuteriation and 1-13C labeling studies of acetyl cedrene. The key step involves cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement.

KW - acetyl cedrene

KW - reaction mechanism

KW - deuterium exchange

KW - 13C labelling

KW - follower

KW - biosynthetic pathway

KW - α -cedrene

KW - deuterium exchange

KW - acetylation

KW - cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement (CCR)

U2 - 10.1007/s10600-017-2085-1

DO - 10.1007/s10600-017-2085-1

M3 - Journal article

VL - 53

SP - 661

EP - 664

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 4

ER -