The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic

Tatsuta, Kuniaki; Tanaka, Hiroaki; Tsukagoshi, H.; Kashima, Takafumi; Hosokawa, Seijiro

doi:10.1016/j.tetlet.2010.08.035

Cited by 32 publications

(14 citation statements)

References 25 publications

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“…[10] In 2010, Tastuta et al reported the first total synthesis of lactonamycin (1) by using a sequential intramolecular conjugate addition reaction, a stereoselective glycosidation, and a Michael-Dieckmanntype cyclization as key steps. [11] We reported the model studies on the synthesis of the ABCD rings by using several iterative Michael addition reactions and oxidations to construct the oxygenated lactone entity.…”

Section: Introductionmentioning

confidence: 99%

Studies on the Total Synthesis of Lactonamycin: Synthesis of the Fused Pentacyclic B–F Ring Unit

et al. 2011

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Section: Introductionmentioning

confidence: 99%

Studies on the Total Synthesis of Lactonamycin: Synthesis of the Fused Pentacyclic B–F Ring Unit

et al. 2011

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“…The first total synthesis of lactonamycin (±)‐ 14 in racemic form was achieved by Tatsuta's group in 2010 (Scheme ) . Retrosynthetically, a tandem Michael addition – Dieckman cyclization between furofuranone decorated benzoquinone 217 and benzylic sulfone 218 was envisaged as a convergent assembly of the entire natural product.…”

Section: Total Synthesis Of Furo[32‐b]furanone Natural Productsmentioning

confidence: 99%

“…The first total synthesis of lactonamycin (�)-14 in racemic form was achieved by Tatsuta's group in 2010 (Scheme 29). [67] Retrosynthetically, a tandem Michael addition -Dieckman cyclization between furofuranone decorated benzoquinone 217 and benzylic sulfone 218 was envisaged as a convergent assembly of the entire natural product. For the synthesis of benzoquinone partner 217, the readily prepared benzoquinone monoketal 220 was subjected to dihydroxylation, stereoselective carbonyl reduction and regioselective OTBS-protection to give 221.…”

Section: Tatsuta Synthesis Of (�)-Lactonamycin (14)mentioning

confidence: 99%

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

et al. 2020

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The ubiquitous presence of highly oxygenated furo[3,2‐b]furanone fragments in diverse natural products with wide range of biological activities such as anti‐cancer, anti‐HIV, anti‐microbial activities, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Enticed by their potent biological activities and challenging polycyclic architecture, total synthesis of furo[3,2‐b]furanone natural products has witnessed intense activity in recent years with many notable achievements in the synthesis of structurally embellished family of bioactive metabolites such as plakortones, lactonamycines, schisanartanes, etc. While presenting a comprehensive account of post‐2000 syntheses of these natural products, through strategic and nuanced use of modern tools of organic synthesis, this review also aims to stimulate interest in exploring the diversity space around these natural products for newer applications.

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“…The group of Danishefsky was the first to report a diastereoselective synthesis of lactonamycinone ( 214 ) employing a Diels–Alder reaction [162–163]. In 2010, Tastuta completed the first total synthesis of lactonamycin ( 215 ) by using a sequential conjugate addition, a stereoselective glycosylation reaction and a Michael–Dieckmann-type cyclization [164]. The recently published total synthesis of lactonamycin ( 215 ) and lactonamycin Z ( 217 ) by Saikawa and Nakata is based on a late-stage glycosylation strategy (Scheme 29).…”

Section: Reviewmentioning

confidence: 99%

The chemistry of isoindole natural products

Speck¹,

Magauer²

2013

Beilstein J. Org. Chem.

316

163

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SummaryThis review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples. Within different congeners, we have selected a few members and discussed the synthetic routes in more detail. The putative biosynthetic pathways of the presented isoindole alkaloids are described as well.

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The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic

Cited by 32 publications

References 25 publications

Studies on the Total Synthesis of Lactonamycin: Synthesis of the Fused Pentacyclic B–F Ring Unit

Studies on the Total Synthesis of Lactonamycin: Synthesis of the Fused Pentacyclic B–F Ring Unit

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

The chemistry of isoindole natural products

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