Methodology for the synthesis of 11,13-dihydroxy gibberellins

Jianping Liu; Lewis N. Mander; Masaji Koshioka

Methodology for the synthesis of 11,13-dihydroxy gibberellins

Jianping Liu, Lewis N. Mander^*, Masaji Koshioka

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

A general procedure has been established for the synthesis of 11,13-dihydroxy gibberellins. The key steps involve the isomerization of the 19,10 lactone functionality to the 19,2-isomer, bromination at C-1 and C-11, then selective nucleophilic displacement of the 11-bromo substituent by acetate with silver(1) acetate. Reconstitution of the 19,10 lactone functionality was effected by bromolactonization of a Δ⁹-ene 19-carboxylic acid to give a 9β-bromo 19,10-lactone followed by stereoselective hydrogenolysis of the bromo substituent.

Original language	English
Pages (from-to)	68-79
Number of pages	12
Journal	Arkivoc
Volume	2004
Issue number	10
Publication status	Published - 11 Jun 2004

Cite this

@article{b9397a6de1744a1282050c23234094b3,

title = "Methodology for the synthesis of 11,13-dihydroxy gibberellins",

abstract = "A general procedure has been established for the synthesis of 11,13-dihydroxy gibberellins. The key steps involve the isomerization of the 19,10 lactone functionality to the 19,2-isomer, bromination at C-1 and C-11, then selective nucleophilic displacement of the 11-bromo substituent by acetate with silver(1) acetate. Reconstitution of the 19,10 lactone functionality was effected by bromolactonization of a Δ9-ene 19-carboxylic acid to give a 9β-bromo 19,10-lactone followed by stereoselective hydrogenolysis of the bromo substituent.",

keywords = "11-Hydroxy-gibberellins, Bromo-lactonization, Loquat, Nucleophilic substitution, Silver ion",

author = "Jianping Liu and Mander, {Lewis N.} and Masaji Koshioka",

year = "2004",

month = jun,

day = "11",

language = "English",

volume = "2004",

pages = "68--79",

journal = "Arkivoc",

issn = "1551-7004",

publisher = "Arkat USA",

number = "10",

}

TY - JOUR

T1 - Methodology for the synthesis of 11,13-dihydroxy gibberellins

AU - Liu, Jianping

AU - Mander, Lewis N.

AU - Koshioka, Masaji

PY - 2004/6/11

Y1 - 2004/6/11

N2 - A general procedure has been established for the synthesis of 11,13-dihydroxy gibberellins. The key steps involve the isomerization of the 19,10 lactone functionality to the 19,2-isomer, bromination at C-1 and C-11, then selective nucleophilic displacement of the 11-bromo substituent by acetate with silver(1) acetate. Reconstitution of the 19,10 lactone functionality was effected by bromolactonization of a Δ9-ene 19-carboxylic acid to give a 9β-bromo 19,10-lactone followed by stereoselective hydrogenolysis of the bromo substituent.

AB - A general procedure has been established for the synthesis of 11,13-dihydroxy gibberellins. The key steps involve the isomerization of the 19,10 lactone functionality to the 19,2-isomer, bromination at C-1 and C-11, then selective nucleophilic displacement of the 11-bromo substituent by acetate with silver(1) acetate. Reconstitution of the 19,10 lactone functionality was effected by bromolactonization of a Δ9-ene 19-carboxylic acid to give a 9β-bromo 19,10-lactone followed by stereoselective hydrogenolysis of the bromo substituent.

KW - 11-Hydroxy-gibberellins

KW - Bromo-lactonization

KW - Loquat

KW - Nucleophilic substitution

KW - Silver ion

UR - http://www.scopus.com/inward/record.url?scp=5044221615&partnerID=8YFLogxK

M3 - Article

SN - 1551-7004

VL - 2004

SP - 68

EP - 79

JO - Arkivoc

JF - Arkivoc

IS - 10

ER -

Methodology for the synthesis of 11,13-dihydroxy gibberellins

Abstract

Other files and links

Fingerprint

Cite this