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

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

doi:10.1007/s10600-017-2085-1

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

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

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer 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.

Originalsprog	Engelsk
Tidsskrift	Chemistry of Natural Compounds
Vol/bind	53
Udgave nummer	4
Sider (fra-til)	661-664
Antal sider	4
ISSN	0009-3130
DOI	https://doi.org/10.1007/s10600-017-2085-1
Status	Udgivet - 2017

Emneord

13C labelling
acetyl cedrene
deuterium exchange
follower
reaction mechanism

Link til dokument

10.1007/s10600-017-2085-1

Citer dette

@article{d20c5712ccf341db98a0885f48a215f4,

title = "Multi-step rearrangement mechanism for acetyl cedrene to the hydrocarbon follower",

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.",

keywords = "13C labelling, acetyl cedrene, deuterium exchange, follower, reaction mechanism, acetylation , biosynthetic pathway, cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement (CCR) , deuterium exchange, α -cedrene , acetylation, cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement (CCR), α -cedrene",

author = "Paknikar, {Shashikumar Keshav} and Kamounah, {Fadhil S.} and Hansen, {Poul Erik} and Wadia, {Murzban Sorab}",

year = "2017",

doi = "10.1007/s10600-017-2085-1",

language = "English",

volume = "53",

pages = "661--664",

journal = "Chemistry of Natural Compounds",

issn = "0009-3130",

publisher = "Springer New York LLC",

number = "4",

}

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 - 13C labelling

KW - acetyl cedrene

KW - deuterium exchange

KW - follower

KW - reaction mechanism

KW - acetylation

KW - biosynthetic pathway

KW - cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement (CCR)

KW - deuterium exchange

KW - α -cedrene

KW - acetylation

KW - cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement (CCR)

KW - α -cedrene

U2 - 10.1007/s10600-017-2085-1

DO - 10.1007/s10600-017-2085-1

M3 - Journal article

SN - 0009-3130

VL - 53

SP - 661

EP - 664

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

IS - 4

ER -