First Synthesis of (+)‐α‐ and (+)‐γ‐Polypodatetraenes.

Kinoshita, Masako; Ohtsuka, Mahisa; Nakamura, Daisuke; Akita, Hiroyuki

doi:10.1002/chin.200301177

Cited by 2 publications

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“…Akita et al previously reported the total synthesis of (-)-drimenol based on enzymatic resolution [20], and in the same report, homodrimenol 124 was described as derived from drimenol. Starting from 124, Akita et al [61] carried out the first synthesis of (+)--polypodatetraene. The elongation of the carbon chain from the primary alcohol group of 124 was achieved by bromination and subsequent Drimenol: A versatile synthon Natural Product Communications Vol.…”

Section: Drimenol As Natural Chiral Synthon For Ambergris Related Compoundsmentioning

confidence: 99%

“…Hydroxylation at the 1 position is a distinctive characteristic of several natural bioactive terpenic compounds, such as forskolin (106) a potent inhibitor of adenylcyclase, mentioned before. Aranda et al [61] described that a simple reaction sequence can result, in few steps, in the preparation of 1α-hydroxylated compounds in good yields starting from 3β-hydroxy derivatives. The hemisynthesis of 1α-hydroxy drimenol involves the use of acetonide 83 previously reported [46], to protect and then regenerate, when appropriate, the 7,8-double bond.…”

Section: Drimenol In Microbiological Hydroxylationsmentioning

confidence: 99%

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Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

Cortés

Delgado

Saitz

et al. 2011

Natural Product Communications

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Several reviews have been published on sesquiterpenes, and on drimane-type sesquiterpenes, going through drimenol and related compounds among others. However, to our knowledge, this is the first review exclusively on drimenol. Although, the main focus is on drimenol as a synthon for other drimane-type compounds, synthetic routes to obtain racemic and (-)-drimenol are summarized, as well as its isolation and determination of its configuration, in the early fifties. The reviewed synthetic routes start from natural (-)-drimenol as chiral synthon in most of cases, nevertheless total syntheses are considered as well. The strategies where racemic drimenol is involved begin with biomimetic cyclization of trans-farnesol. Microbiological procedures to functionalize the A ring of drimenol are also commented. The revision is classified according to the chemical structure of the final product, which mainly correspond to structures of natural occurrence, although other related derivatives are also analyzed.

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Section: Drimenol As Natural Chiral Synthon For Ambergris Related Compoundsmentioning

confidence: 99%

Section: Drimenol In Microbiological Hydroxylationsmentioning

confidence: 99%

Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

Cortés

Delgado

Saitz

et al. 2011

Natural Product Communications

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“…ました．16,18,19) これらの中に生理活性を有する化合物も多く，(8aS )-albaconol 20) と(-)-BE-40644 の絶対構造は全合成することにより決定することができました． 21) 一方，(8aR )-24 からは(8aR )-copalic acid と(8aR)-copalol が合成されました(Fig. 6) ． 17) 次に高価な動物性香料である ( ＋ ) -ambrein 27 (Fig.…”

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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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First Synthesis of (+)‐α‐ and (+)‐γ‐Polypodatetraenes.

Abstract: Terpenes Terpenes U 0200First Synthesis of (+)-α-and (+)-γ-Polypodatetraenes. -(KINOSHITA, M.; OHTSUKA, M.; NAKAMURA, D.; AKITA*, H.; Chem. Pharm. Bull. 50 (2002) 7, 930-934; Sch. Pharm. Sci., Toho Univ., Funabashi, Chiba 274, Japan; Eng.) -D. Singer 01-177

Cited by 2 publications

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Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

Natural Products Syntheses Based on the Biotransformation Using Biocatalyst

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