Chemoenzymatic Synthesis of (+)-.ALPHA.-Polypodatetraene and Methyl (5R,10R,13R)-Labda-8-en-15-oate

Kinoshita, Masako; Miyake, Takahiro; Arima, Yuusuke; Oguma, Minako; Akita, Hiroyuki

doi:10.1248/cpb.56.118

Cited by 3 publications

(4 citation statements)

References 15 publications

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“…Optically active title compound (29) was considered to be an important chiral intermediate for the synthesis of drimane type natural products and the racemic substrate for enzymatic resolution was synthesized from (±)-linalool (25) as shown in Scheme 4. 14 Heating of 25 and ethyl vinyl ether in the presence of H 3 PO 4 followed by acid treatment gave a mixture of aldehyde (26), which was reacted with…”

Section: Hydroxydecahydro-558a-trimethylnaphthalene-1-carboxylate Amentioning

confidence: 99%

“…24 Straightforward synthesis of (+)-80 from (+)-albicanol (64) was shown in Scheme 11. 25 Mesylation of (+)-64 followed by treatment with benzenethiolate ion gave sulfide (8aS)-77 in 74% overall yield from (+)-64. Oxidation of (8aS)-77 with 30% H 2 O 2 in the presence of Mo 7 O 24 (NH 4 ) 6 ·4H 2 O afforded sulfone (8aS)-78 in 90% yield, which was lithiated with LDA followed by treatment with (E,E)-farnesyl bromide to give a diastereomeric mixture of (8aS)-79 in 83% yield.…”

Section: Syntheses Of (+)--Polypodatetraene (-)-Copalic Acid and (-mentioning

confidence: 99%

“…We tried to synthesize methyl (5R,10R,13R)-labda-8-en- 15-oate (133) corresponding to the left carboxylic acid part of the above mentioned terpenoid glyceryl ester as shown in Scheme 18. 25 Target molecule (133) could be obtained by coupling reaction of (8aR)-bicyclofarnesyl bromide (130) and chiral isoprene unit (S)-131. 25 (8aR)-Bicyclofarnesol (67) was obtained from (8aR)-62 by the same way as the preparation of (±)-67 from (±)-62 as shown in Scheme 9 and was treated with PBr 3 to give (8aR)-130.…”

Section: Synthesis Of Methyl (5r10r13r)-labda-8-en-15-oatementioning

confidence: 99%

“…25 Target molecule (133) could be obtained by coupling reaction of (8aR)-bicyclofarnesyl bromide (130) and chiral isoprene unit (S)-131. 25 (8aR)-Bicyclofarnesol (67) was obtained from (8aR)-62 by the same way as the preparation of (±)-67 from (±)-62 as shown in Scheme 9 and was treated with PBr 3 to give (8aR)-130. Treatment of (S)-131 with lithium diisopropylamide (LDA) gave the corresponding anion, which was subjected to the coupling reaction with (8aR)-130 to afford the coupling product (132) in 70% overall yield from (8aR)-67.…”

Section: Synthesis Of Methyl (5r10r13r)-labda-8-en-15-oatementioning

confidence: 99%

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Recent Advances in the Syntheses of Decalin Type Natural Products

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Section: Hydroxydecahydro-558a-trimethylnaphthalene-1-carboxylate Amentioning

confidence: 99%

Section: Syntheses Of (+)--Polypodatetraene (-)-Copalic Acid and (-mentioning

confidence: 99%

Section: Synthesis Of Methyl (5r10r13r)-labda-8-en-15-oatementioning

confidence: 99%

Section: Synthesis Of Methyl (5r10r13r)-labda-8-en-15-oatementioning

confidence: 99%

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Recent Advances in the Syntheses of Decalin Type Natural Products

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Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base

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Natural Products Syntheses Based on the Biotransformation Using Biocatalyst

Akita

2011

YAKUGAKU ZASSHI

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This review summarizes the chemoenzymatic synthesis of the biologically active natural products based on a combination of chemical diastereoselectivity and enzymatic enantioselectivity using biocatalyst. Asymmetric reduction of 2-methyl-3-keto ester with yeast gave the optically active syn-2-methyl-3-hydroxy ester, which was converted to natural product such as (-)-oudemansin B. Asymmetric hydrolysis of 3-acetoxy-2-methy esters possessing syn-or anti-structure aŠorded the optically active 3-hydroxy-2-methyl esters and 3-acetoxy-2-methy esters corresponding to the starting material. One of these optically active 3-hydroxy-2-methyl esters was converted to aglycone of macrolide, venturicidins A and B possessing 10 chiral centers. Both primary alcohols possessing a chiral center at b-position of hydroxyl group and secondary alcohols were subjected to the lipase-assisted acylation in the presence of acyl donor to aŠord the optically active esters and the optically active alcohols corresponding to the starting material. These optically active compounds were converted to the biologically active natural products such as bisabolane type sesquiterpenes, decaline type diterpenes or triterpenes, nikkomycin B, (＋)-asperlin, (-)-chuangxinmycin, (-)-indolmycin, cystothiazoles melithiazols, myxothiazols and piericidins possessing antifungal and cytotoxicic activities, inhibition of NADH oxidation, etc. Reaction of primary alcohol and glucose using immobilized b-glucosidase gave alkyl b-glucosides in high yield. Pentaacetate of allyl b-glucoside was subjected to Mizoroki-Heck type reaction with phenylboronic acid derivatives to give phenylpropenoid b-D-glucopyranosid congeners.

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Chemoenzymatic Synthesis of (+)-.ALPHA.-Polypodatetraene and Methyl (5R,10R,13R)-Labda-8-en-15-oate

Cited by 3 publications

References 15 publications

Recent Advances in the Syntheses of Decalin Type Natural Products

Recent Advances in the Syntheses of Decalin Type Natural Products

Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base

Natural Products Syntheses Based on the Biotransformation Using Biocatalyst

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