Abstract
Lipase-catalyzed site-selective deacetylation of 2,5-dimethylnaphthalene-l,4-diol diacetate was examined. With Candida antarctica lipase B, the suppressing effect of a methyl substituent at the peri-position of the a-naphthyl ester over that at the ortho-position was significant. This site-selectivity was in contrast to that of chemical hydrolysis reported to date. From the resulting monoacetate, mansonone F, a physiologically active heterocyclic orthoquinone, was synthesized in 38% yield in as few as three steps.
| Original language | English |
|---|---|
| Pages (from-to) | 625-632 |
| Number of pages | 8 |
| Journal | Heterocycles |
| DOIs | |
| Publication status | Published - 2019 Jan 1 |
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ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
Cite this
Lipase-catalyzed site-selective deacetylation of sterically hindered naphthohydroquinone diacetate and its application to the synthesis of a heterocyclic natural product. / Hashimoto, Riichi; Sakakura, Ayaka; Hanaya, Kengo; Higashibayashi, Shuhei; Sugai, Takeshi.
In: Heterocycles, 01.01.2019, p. 625-632.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Lipase-catalyzed site-selective deacetylation of sterically hindered naphthohydroquinone diacetate and its application to the synthesis of a heterocyclic natural product
AU - Hashimoto, Riichi
AU - Sakakura, Ayaka
AU - Hanaya, Kengo
AU - Higashibayashi, Shuhei
AU - Sugai, Takeshi
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Lipase-catalyzed site-selective deacetylation of 2,5-dimethylnaphthalene-l,4-diol diacetate was examined. With Candida antarctica lipase B, the suppressing effect of a methyl substituent at the peri-position of the a-naphthyl ester over that at the ortho-position was significant. This site-selectivity was in contrast to that of chemical hydrolysis reported to date. From the resulting monoacetate, mansonone F, a physiologically active heterocyclic orthoquinone, was synthesized in 38% yield in as few as three steps.
AB - Lipase-catalyzed site-selective deacetylation of 2,5-dimethylnaphthalene-l,4-diol diacetate was examined. With Candida antarctica lipase B, the suppressing effect of a methyl substituent at the peri-position of the a-naphthyl ester over that at the ortho-position was significant. This site-selectivity was in contrast to that of chemical hydrolysis reported to date. From the resulting monoacetate, mansonone F, a physiologically active heterocyclic orthoquinone, was synthesized in 38% yield in as few as three steps.
UR - http://www.scopus.com/inward/record.url?scp=85069663626&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85069663626&partnerID=8YFLogxK
U2 - 10.3987/COM-18-S(F)12
DO - 10.3987/COM-18-S(F)12
M3 - Article
AN - SCOPUS:85069663626
SP - 625
EP - 632
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
ER -