Total synthesis of progesterone receptor ligands, (−)-PF1092A, B and C

Tatsuta, Kuniaki; Yasuda, Shohei; Kurihara, Kenichi; Toko, Kiyoshi; Shinei, Rie; Okonogi, Tsuneo

doi:10.1016/s0040-4039(97)00042-7

Cited by 36 publications

(13 citation statements)

References 9 publications

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“…[11] Compound 38 was silylated to produce, as expected, the labile enol silyl ether 39 having a simultaneously silylated hydroxy group. The SnCl 4 -promoted cyclization of 39 resulted in the formation of the cyclohexenone 40.…”

Section: Total Synthesis Of Glyoxalase I Inhibitor and Its Precursor mentioning

confidence: 64%

“…The first synthesis was achieved by Vasella et al in which methyl a-d-glucopyranoside was effectively used as starting material. [14] As mentioned in the synthesis of the PF1092s (34±36), [11] the SnCl 4 -promoted, aldol-like cyclization of phenylsulfonyl enol silyl ethers containing a dimethyl acetal has been explored extensively in our laboratories. This transformation is ideally suited to the synthesis of carbocycle-containing natural products and carbasugars, since the core skeleton arises after appropriate replacement of the phenylsulfonyl group.…”

Section: Total Synthesis Of Glyoxalase I Inhibitor and Its Precursor mentioning

confidence: 99%

“…[11] Both pseudo-aminosugars 49 and 53 were also isolated from the fermentation broth of Streptomyces hygroscopicus subsp. limoneus IFO 12703 and found to show some biological activities.…”

Section: Novel Syntheses Of the Natural Pseudoaminosugars (+)-Valienamentioning

confidence: 99%

“…Structurally, they belong to the complex eremophilane-type sesquiterpenes, with four contiguous cis-substituents on an octalone skeleton fused with a butenolide ring. [11] The first enantiospecific total synthesis of (±)-PF1092A, B, and C (34±36) is based on the SnCl 4 -promoted cyclization of an a-keto methyl sulfone and dimethyl acetal followed by a Stork annulation which gives the octalone core (Scheme 3). [11] The critical step was the direct opening of the furanose ring (28 to 29) by silylation with simultaneous formation of the enol silyl ether, because the one-step opening of the furanose ring is generally difficult.…”

Section: Introductionmentioning

confidence: 99%

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Total Syntheses of Useful Bioactive Compounds

Tatsuta

2001

Adv. Synth. Catal.

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The first total syntheses of a variety of useful bioactive compounds have been accomplished by practically useful strategies. In addition practically useful intermediates have been developed, analogues of natural products have been prepared, their structure‐activity relationships studied, and the large‐scale preparations of medically useful compounds established. The target molecules are antibiotics, antifungals, antitumor antibiotics, compounds related to β‐lactam antibiotics, enzyme inhibitors, central nervous system‐affecting products, non‐steroidal progesterone receptor ligands, mussel‐attachment inhibitors, and so on.

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Section: Total Synthesis Of Glyoxalase I Inhibitor and Its Precursor mentioning

confidence: 64%

Section: Total Synthesis Of Glyoxalase I Inhibitor and Its Precursor mentioning

confidence: 99%

“…[11] Both pseudo-aminosugars 49 and 53 were also isolated from the fermentation broth of Streptomyces hygroscopicus subsp. limoneus IFO 12703 and found to show some biological activities.…”

Section: Novel Syntheses Of the Natural Pseudoaminosugars (+)-Valienamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Total Syntheses of Useful Bioactive Compounds

Tatsuta

2001

Adv. Synth. Catal.

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“…The lactone 84 was methylated stereoselectively by Michael addition with MeMgBr [112,113] in the presence of CuBr Á Me 2 S and TMSCl to give 102 as a single isomer. Reduction with LiAlH 4 afforded acyclic diol 103, which was transformed to give the segment 104 in several steps.…”

Section: The Total Synthesis Of Cochleamycin Amentioning

confidence: 99%

Total syntheses of bioactive natural products from carbohydrates

Tatsuta

Hosokawa

2006

Science and Technology of Advanced Materials

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Total syntheses of bioactive natural products recently accomplished in our laboratories are described. They are classified by structures of target molecules and are focused on our original approach to their own structures. The target molecules include nanaomycin, kalafungin, BE-54238B, tetracycline, rosmarinecine, thienamycin, luminacines C 1 and C 2 , tetrodecamycin, cochleamycin A, and tubelactomicin A, which have been synthesized as optically pure form from carbohydrates.

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Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

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The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

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Total synthesis of progesterone receptor ligands, (−)-PF1092A, B and C

Cited by 36 publications

References 9 publications

Total Syntheses of Useful Bioactive Compounds

Total Syntheses of Useful Bioactive Compounds

Total syntheses of bioactive natural products from carbohydrates

Desulfonylation Reactions

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