183202-73-5

Usage

Uses

Used in Pharmaceutical Industry:
KENDOMYCIN is used as an antibacterial agent for its potent activity against a broad spectrum of bacteria, including antibiotic-resistant strains such as MRSA. Its effectiveness against both Gram-positive and Gram-negative bacteria makes it a valuable asset in the fight against bacterial infections.
Used in Oncology:
KENDOMYCIN is used as an antitumor agent due to its demonstrated cytotoxic effects on several carcinoma cell lines. It modulates various oncological signaling pathways, potentially leading to the inhibition of tumor growth and progression.
Used in Orthopedics:
KENDOMYCIN is used as an antiosteoporotic agent, with its antiosteoporotic activities potentially beneficial in the treatment and prevention of bone loss associated with osteoporosis.
Used in Drug Development:
KENDOMYCIN is used as a lead compound in the development of new drugs, particularly in the areas of antibacterial, antitumor, and antiosteoporotic therapies, owing to its diverse range of biological activities and unique chemical structure.

InChI:InChI=1/C32H61N13O9/c1-15(2)13-19(33)25(48)42-21(10-8-12-39-32(36)37)27(50)43-20(9-7-11-38-31(34)35)26(49)40-17(5)24(47)44-22(14-46)28(51)45-23(16(3)4)29(52)41-18(6)30(53)54/h15-23,46H,7-14,33H2,1-6H3,(H,40,49)(H,41,52)(H,42,48)(H,43,50)(H,44,47)(H,45,51)(H,53,54)(H4,34,35,38)(H4,36,37,39)

Upstream product

• 1220044-85-8 C₃₅H₅₆O₆Si 
• 808766-03-2 tert-Butyl-[2-((1S,3S)-4-iodo-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-dimethyl-silane 
• 808766-16-7 (2S,4S)-4-[5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-7-methyl-benzofuran-2-yl]-2-methyl-pentan-1-ol 
• 754239-25-3 (1'R,2'R,2S,4S)-5-benzyloxy-2,4-dimethylpentanoic acid (2'-hydroxy-1'-methyl-2'-phenylethyl)methylamide 
• 808766-12-3 tert-butyl-(4-methyl-hept-5-ynyloxy)-diphenyl-silane 
• 808765-99-3 4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-methoxy-2-methyl-phenol 
• 808765-95-9 (3R,4S,5R,6R)-4-Hydroxy-6-((E)-(S)-5-iodo-3-methyl-hex-4-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one 
• 808766-15-6 5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde 
• 808765-98-2 (3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-2-one 
• 808766-01-0 (2S,4S)-5-Benzyloxy-2,4-dimethyl-pentanoic acid 
• 808766-13-4 4-methylhept-5-yn-1-ol 
• 808765-96-0 (S)-4-methylhept-5-ynal 
• 622852-28-2 2,5-dihydroxy-4-methoxy-3-methyl-benzaldehyde 
• 199008-86-1 (S)-5-(tert-butyldiphenylsilyloxy)-2-methylpentanal 

Relevant academic research and scientific papers

Synthesis and biological evaluation of kendomycin and its analogues

Ansa compounds are gifts from microbes with intriguing molecular structures and highly potent bioactivities. One of the ansa compounds, kendomycin, has an oxa-metacyclophane skeleton with a quinone methide core and a fully substituted tetrahydropyran ring. Beyond a common synthetic strategy for construction of the ansa skeleton (i.e., elongation of an alkyl chain from an aromatic core followed by macrocyclization), we challenged a new method for construction of the ansa skeleton via simultaneous macrocyclization and benzannulation (using an intramolecular D?tz benzannulation). Understanding the reactivity of various Fischer-type ω-alkynyloxy chromium carbene complexes with kendomycin analogue syntheses led to achievement of the total synthesis of kendomycin. Investigations of structure-activity relationships revealed the need for an ansa skeleton for antimicrobial activity. Therefore, we envisage that this intramolecular D?tz benzannulation will enable divergent syntheses of ansa compounds which have important bioactive potential.

Total synthesis of the antibiotic kendomycin: A macrocyclization using the Tsuji-Trost etherification

A highly stereocontrolled, convergent total synthesis of kendomycin [(-)-TAN2162], an ansa-macrocyclic antibiotic, is reported. The key of the strategy is an unprecedented Tsuji-Trost macrocyclic etherification, followed by a transannular Claisen rearrangement to construct the 18-membered carbocyclic framework. The oxa-six- and five-membered rings were also stereoselectively constructed respectively by a cascade oxidative cyclization at an unfunctionalized benzylic position and using a one-pot epoxidation/5-exo-tet epoxide opening. A new construct: The asymmetric total synthesis of the antibiotic kendomycin was accomplished by using a highly stereocontrolled convergent route. The key feature of the synthetic strategy is the construction of an 18-membered carbocycle based on an intramolecular Tsuji-Trost etherification/transannular Claisen rearrangement sequence. TBS=tert- butyldimethylsilyl.

Total synthesis of kendomycin featuring intramolecular doetz benzannulation

One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Doetz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

Ring-closing metathesis and photo-fries reaction for the construction of the ansamydn antibiotic kendomycin: Development of a protecting group free oxidative endgame

Two convergent total synthe-ses of the ansa-polyketide (-)-kendo-mycin (1) are described. The syntheses benefit from the use of readily avail-able and cheap starting materials. Highly complex diastereoselective Claisen-Ireland rearrangements were used to introduce the (E)-double bond and the C16-Me group. The ring clo-sure of the strained ansa macrocycle was achieved by ring-closing metathesis and a highly efficient combination of macrolactonization and photo-Fries re-action. A protecting group free end-game via an unstable o-quinone is pre-sented. Additionally some unsuccessful synthetic efforts towards the total synthesis of 1 are described.

Total synthesis of (-)-kendomycin

(Chemical Equation Presented) An enantioselective synthesis of (-)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a-C10 fragment. An underutilized samarium(II) iodide

Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy

A convergent stereocontrolled total synthesis of (-)-kendomycin (1) has been achieved. The synthesis proceeds with a longest linear sequence of 21 steps, beginning with commercially available 2,4-dimethoxy-3-methylbenzaldehyde (12). Highlights of the synthesis include an effective Petasis-Ferrier union/rearrangement tactic to construct the sterically encumbered tetrahydropyran ring, a ring-closing metathesis to generate the C(4a-13-20a) macrocycle, an effective epoxidation/deoxygenation sequence to isomerize the C(13,14) olefin, and a biomimetic quinone-methide-lactol assembly to complete the synthesis.

Total synthesis of (-)-kendomycin exploiting a petasis-ferrier rearrangement/ring-closing olefin metathesis synthetic strategy

The total synthesis of (-)-kendomycin (1), a novel macrocyclic polyketide with antibacterial and antitumor activity, was achieved in 21 steps (longest linear sequence) exploiting an effective Petasis-Ferrier union/rearrangement tactic to construct the tet

Total synthesis of kendomycin: A macro-C-glycosidation approach

Kendomycin, also known as (-)-TAN 2162, is a novel polyketide-derived ansamycin isolated from Streptomyces sp., which exhibits potent antagonist and agonist activities at the endothelin and calcitonin receptors, respectively. This bacterial metabolite als