Synthetic Study of C1-C13 Intermediate in Phoslactomycins and Leustroducsins.

Phoslactomycins and leustroducsins are highly functionalized polyketides. In this paper, we report the new synthetic method for the C1-C13 fragment. This method involves a Suzuki-Miyaura coupling reaction between the C3-C7 acetylene and C8-C13 iodoolefin, followed by construction of the lactone part. The C8-C9 diol is constructed by dihydroxylation in the late stage of the synthesis.

• Publication year

  2026

• Venue

  Chemical and pharmaceutical bulletin

• Publication date

  2026-01-14

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1248/cpb.c25-00714PMID 41535000
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Synthesis of Phoslactomycin I-i.

  2025cited by this paper
• Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

  2022cited by this paper
• Total Synthesis of Kalimantacin A.

  2020cited by this paper
• Gold-catalyzed Hosomi-Sakurai type reaction for the total synthesis of herboxidiene.

  2016cited by this paper
• Paleo-soraphens: chemical total syntheses and biological studies.

  2015cited by this paper
• A Highly Convergent Total Synthesis of Leustroducsin B

  2015cited by this paper
• Callipeltosides A, B and C: Total Syntheses and Structural Confirmation

  2015cited by this paper
• Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation.

  2013cited by this paper
• Total synthesis of (-)-goniotrionin.

  2012cited by this paper
• Directing group-controlled hydrosilylation: regioselective functionalization of alkyne.

  2011cited by this paper
• Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

  2011cited by this paper
• Good timing in total synthesis: the case of phoslactomycin A.

  2010cited by this paper
• A convergent approach toward the C1-C11 subunit of phoslactomycins and formal synthesis of phoslactomycin B.

  2009cited by this paper
• Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B.

  2009cited by this paper
• Total synthesis of phoslactomycin A.

  2009cited by this paper
• Total synthesis of leustroducsin B.

  2008cited by this paper
• Total synthesis of solandelactones A, B, E, and F exploiting a tandem Petasis-Claisen lactonization strategy.

  2008cited by this paper
• Asymmetric total synthesis of (+)-phoslactomycin B.

  2008cited by this paper
• Hexafluoroisopropanol as a unique solvent for stereoselective iododesilylation of vinylsilanes.

  2008cited by this paper
• Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons

  2007cited by this paper
• Total synthesis of phoslactomycin B and its biosynthetic deamino precursor.

  2006cited by this paper
• A practical and efficient synthesis of the C-16-C-28 spiroketal fragment (CD) of the spongistatins.

  2003cited by this paper
• Total synthesis of leustroducsin B.

  2003cited by this paper
• Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers.

  2002cited by this paper
• An Alternative Approach for the Conversion of Aldehydes to Terminal Alkynes.

  1999cited by this paper
• Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner-Emmons Reagents, Ethyl (Diarylphosphono)acetates.

  1997cited by this paper
• Novel microbial metabolites of the phoslactomycins family induce production of colony-stimulating factors by bone marrow stromal cells. I. Taxonomy, fermentation and biological properties.

  1993cited by this paper
• Isolation and structure of phosphazomycin C.

  1990cited by this paper
• Studies on new phosphate ester antifungal antibiotics phoslactomycins. II. Structure elucidation of phoslactomycins A to F.

  1989cited by this paper
• Studies on new phosphate ester antifungal antibiotics phoslactomycins. I. Taxonomy, fermentation, purification and biological activities.

  1989cited by this paper
• A new antifungal antibiotic, phosphazomycin A.

  1985cited by this paper

• No citing papers are available for this paper.