Determination of the absolute configuration of the cytotoxic natural product pericosine D

Usami, Yoshihide; Mizuki, Koji; Ichikawa, Hayato; Arimoto, Masao

doi:10.1016/j.tetasy.2008.06.008

Cited by 27 publications

(37 citation statements)

References 18 publications

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“…Structural determinations of pericosines D and D o were not straightforward [64][65][66]85]. Isolation of pericosine D was reported in 1999 at the Annual Meeting of the Pharmaceutical Society of Japan, and the structure was reported as 26 [85].…”

Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

“…Detailed reviewing of the NMR data accumulated for structurally related molecules, which are summarized in Fig. 5, was not sufficient to deduce which of these was the true structure of pericosine D. It was therefore clear that the only way to resolve this problem was to carry out total syntheses of both 4 and 44 following the reactions detailed in Scheme 6 [65].…”

Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

“…This was subsequently designated as pericosine D o to indicate the natural product that had originally been referred to as pericosine D. Presumably, a sample mix-up occurred at some stage during the original work, and instead of pericosine D o being converted to the acetonide, it was an unrecognized sample of pericosine D [65].…”

Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

“…This discrepancy may have resulted from mixed up samples of natural products and will be discussed in further detail later in the chapter [65,66]. The originally reported pericosine D was subsequently designated pericosine D o (6).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Marine-Derived Carbasugar Pericosines

Usami

2014

Studies in Natural Products Chemistry

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Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

Section: Syntheses Of Pericosines Strating From D-ribose Via Ring-clomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Marine-Derived Carbasugar Pericosines

Usami

2014

Studies in Natural Products Chemistry

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“…Epoxides are the most useful and versatile substrates in organic synthesis due to their high reactivity [1][2][3][4][5][6]. A number of methods have been reported for the cleavage of epoxides with various nucleophiles, such as carbon-based nucleophiles [7,8], halides [9], and alcohols [10,11].…”

Section: Introductionmentioning

confidence: 99%

Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides

et al. 2010

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This paper presents a versatile reagent for epoxide cleavage. The allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions, respectively. It could also act as a Lewis acid to catalyze the ring opening reactions of epoxides with alcohols.versatile reagent, allyltin tribromide, ring opening of epoxides, room temperature

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Palladium‐Catalyzed Allylic Substitution for the Synthesis of Pericosines

Chung

Angamuthu

et al. 2016

Asian J Org Chem

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As equence of vinylalumination of a-substituted aldehydes,r ing-closingm etathesis (RCM), and palladium-catalyzed allylic substitution was utilized to prepare the biologically active natural products, pericosines, from d-ribose. The anti-adduct of vinylaluminationw as transformed into pericosine Aa fter RCM, removalo ft he 4-methoxybenzyl protect-ing group, and chlorination. The diacetate of the anti-adduct was converted to pericosine Ca fter the palladium-catalyzed, S N 2'-type, allylic substitution. However,a nu nexpected dimeric product was generated in utilizing this approacht o preparep ericosine E. Results and DiscussionRetrosynthetic analysis of the pericosines is shown in Scheme1,w hich indicates that cyclitol 1 is the key intermediate. Furtherm anipulations to the allylic alcohol, such as S N 2, S N 2',o rp alladium-catalyzeds ubstitution reactions, could lead to the target pericosines A, C, andE .C yclitol 1 could be obtained from the RCM reaction of the 1,7-diene 3,d erived from Figure 1. Structure of naturallyo ccurring pericosines.

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Determination of the absolute configuration of the cytotoxic natural product pericosine D

Cited by 27 publications

References 18 publications

Synthesis of Marine-Derived Carbasugar Pericosines

Synthesis of Marine-Derived Carbasugar Pericosines

Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides

Palladium‐Catalyzed Allylic Substitution for the Synthesis of Pericosines

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