Asymmetric total synthesis of (−) podophyllotoxin

Hadimani, S. B.; Tanpure, Rajendra P.; Bhat, Sujata V.

doi:10.1016/0040-4039(96)00937-9

Cited by 46 publications

(17 citation statements)

References 28 publications

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“…Chemical synthesis of the PTOX skeleton is possible [45,46] but the presence of four chiral positions and the transg-lactonic ring hinder commercial production. Four general approaches to the synthesis of PTOX derivatives have been developed, each with several variations and innovations: the oxo-ester route, the dihydroxy acid route, the tandem conjugate addition route or the use of a Diels-Alder reaction [22].…”

Section: Extraction and Synthesismentioning

confidence: 99%

Podophyllotoxin: Current approaches to its biotechnological production and future challenges

Yousefzadi¹,

Sharifi²,

Behmanesh³

et al. 2010

Engineering in Life Sciences

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Many plant‐derived agents are being used to treat cancer, including taxol, vinblastine, vincristine, or camptothecin and podophyllotoxin derivatives, among others. Plant biotechnology can provide a new tool for the production of anticancer agents but in spite of considerable efforts to produce vinblastine and vincristine in cell cultures and knowledge of the biosynthetic pathway of Catharanthus roseus alkaloids, the biotechnological production of taxol has only been achieved at an industrial level by companies such as Phyton Biotech and Cytoclonal Pharmaceutics. Podophyllotoxin was isolated as the active antitumor agent from the roots of Podophyllum species and more recently from the genus Linum and others. Etoposide, teniposide, and etophos are semi‐synthetic derivatives of podophyllotoxin and are used in the treatment of cancer. Biotechnological approaches, including the use of cell cultures, biotransformation, or metabolic engineering techniques to manipulate the biosynthetic pathway, represent an alternative for the production of podophyllotoxin and are discussed in this review.

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Section: Extraction and Synthesismentioning

confidence: 99%

Podophyllotoxin: Current approaches to its biotechnological production and future challenges

Yousefzadi¹,

Sharifi²,

Behmanesh³

et al. 2010

Engineering in Life Sciences

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“…[15] Etoposide (5)t herefore became am ember of the WHOsl ist of essential medicines. Especially the construction of the southern stereocenter with the appropriate configuration has been remarkably difficult through the Friedel-Crafts approach, both chemically [18] and by biotechnological methods. Especially the construction of the southern stereocenter with the appropriate configuration has been remarkably difficult through the Friedel-Crafts approach, both chemically [18] and by biotechnological methods.…”

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confidence: 99%

Chemoenzymatic Total Synthesis of Deoxy‐, epi‐, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

et al. 2019

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Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy‐, epi ‐, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2‐oxoglutarate‐dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non‐natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C−C bond formation by C−H activation or hydroxylation at the benzylic position prone to ring closure.

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“…Application of sulfoxide anions seems to avoid this problem and Bhat has used a chiral sulfoxide in an exceptionally concise asymmetric synthesis of podophyllotoxin (Scheme 2, a). [31] This synthesis is particularly noteworthy as TFA-mediated cyclisation of aryl carbinol 25 followed by sulfoxide hydrolysis afforded podophyllotoxin albeit in low yield. The formation of the desired 1,2-cis stereochemi- Scheme 1. cal arrangement in such an acid-catalysed cyclisation is unusual.…”

Section: C-ring Formation By Aryl Substitutionmentioning

confidence: 99%

Advances in the Synthesis of Aryltetralin Lignan Lactones

Sellars

Steel

2007

Eur J Org Chem

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Etoposide and tenoposide, derivatives of the aryltetralin lignan lactone podophyllotoxin (5), are clinically important anticancer agents. The structure of podophyllotoxin includes four contiguous chiral centres contained within a stereochemically unstable trans‐fused tetrahydronaphthalene lactone skeleton. Reflecting this challenging structure and important biological role there has been long‐standing interest in developing efficient stereocontrolled syntheses of this class of natural product. This microreview summarises the key developments towards this end focussing on more recent developments both from within the authors group and elsewhere.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Asymmetric total synthesis of (−) podophyllotoxin

Cited by 46 publications

References 28 publications

Podophyllotoxin: Current approaches to its biotechnological production and future challenges

Podophyllotoxin: Current approaches to its biotechnological production and future challenges

Chemoenzymatic Total Synthesis of Deoxy‐, epi‐, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Advances in the Synthesis of Aryltetralin Lignan Lactones

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