• Bulletin of the Korean Chemical Society
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• 제22권9호
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• pp.939-940
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• 2001

• Archives of Pharmacal Research
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• 제22권6호
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• pp.624-628
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• 1999

A formal asymmetric synthesis of Mugineic acid was accomplished from cis-2-butene-1,4-diol throughcatalytic Sharpless epoxidation oxidations and doupling reaction.

• 약학회지
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• 제54권6호
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• pp.474-480
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• 2010

Conformationally locked nucleosides are important in searching selective agonists and antagonists for P2Y receptors. There were two previous synthetic works of the crucial intermediate, cyclopentenyl alcohol (3), which had some inefficiency like using too strong dianionic base and synthesis of racemate. Here we describes a facile synthesis of the intermediate using Sharpless epoxidation and the opening of epoxide ring using zinc, followed by Grubb's metathesis as key steps. The intermediate was converted to the southern bicyclo[3.2.0]heptane for confirming its usefulness.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.363.1-363.1
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• 2002

Costunolide. a sesquiterpene lactone is isolated from Magnolia Sieboldi. It is known to possess antitumour and anti-inflammatory activities. This compound is synthesized from Ihe easily available decalin dione using the ring cleavage approach to construct the ten-membered ring system. The two keys points in this work are the chiral inductionon the allyl alcohol moiety using Sharpless epoxidation reaction and opening of the eopxide with an organocuprate reagent which leads to a $\alpha$-exomethylene lactone. (omitted)

• 약학회지
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• 제49권6호
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• pp.443-448
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• 2005

Diosgenin (25 (R) - spirost-5-en-3$\beta$ -ol) was oxidized with 2,3-dichloro -5,6-dicyano-1,4-benzoquinone to form 25(R)-1,4,6-spirostatrien-3-one (1) as rigid cyclic $\alpha$,$\beta$-unsaturated carbonyl compound. This compound was reacted with $H_{2}O_{2}$, m-chloroperoxybenzoic acid (mCPBA), NaOCl in the presence with (R,R)- or (S,S)-Jacobsen catalyst, tert-butyl-hydroperoxide (TBHP) in Mo$(CO)_{6}$, and in VO $(acac)_{2}$ catalyst, respectively, 25(R) -1,4,6-spirostatrien -3-one (1) was reduced with $NaBH_{4}$ L-Selectride, $LiAIH_{4}$,$BH_{3}$ $\cdot$$(CH_{3})_{2}S$, Superhydride, Red-Al, and lithium tri-tert-butoxyaluminium hydride. And 25(R)-4,6-spirostadien-3$\beta$-ol (4) was treated with $H_{2}O_{2}$, mCPBA, TBHP in D - (-) - and L-(+)-diisopropyltar-trate and $Ti(OiPr)_{4}$ condition (Sharpless asymmetric epoxidation), TBHP in $Mo(CO)_{6}$, and in $VO(acac)_{2}$ catalyst, respectively.